Technical field

The present invention relates to the field of perfumery. More particularly, it concerns the use of some derivatives of 2-isobutyl-cyclohexanol or cyclopentanol as defined herein below. These derivatives are useful to confer odor notes of the white flower type.

The present invention concerns some of the compounds as well as the compositions or articles containing said compounds.

Prior art

Several alcohols of the formula (I), wherein R ³ is a hydrogen atom, are known compounds, but all have been reported in the prior art as chemical intermediates. In particular, the cyclopentol of cyclohexanol substituted by a ^1_ Bu group or a (2-methyl-2- propenyl) group (e.g. see US 2376105 or J.O. C., 1997, 62, 1523).

The only exception is 2-(2-methylbutyl)-cyclohexanol or 2-(2-methylpropyl)- cyclohexanol disclosed in JP 02131405 as cockroach repellents. However, said Japanese application, although mentioning that these compounds can be included into a perfume for their cockroach activity (i.e. a perfuming composition), never mentions that the compound has an odor itself or that it can be used as perfuming ingredient to impart a hedonic effect or even an odor.

Furthermore, to the best of our knowledge, all the compounds of formula (II) described herein below are novel.

The closest analogues to the invention's compounds which are known in the prior art as perfuming ingredients are described in Perfumer & Flavorist, 1983, 8 (April/May issue), pg 68. This paper discloses various 2-alkyl-cyclopentanones, and clearly indicates that when the alkyl group comprises a substituent in the first or second carbon (as our invention's alcohol), the odor is rather waxy, oily or rosaceous, i.e. totally different from the one of the present invention. However, this prior art document does not report or suggest any organoleptic properties of the compounds of formula (I), or any use of said compounds in the field of perfumery. Description of the invention

We have now surprisingly discovered that a compound of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein the dotted line represents a carbon-carbon single or double bond; n is 0 or 1 ; and

R ¹ represents a hydrogen atom or a methyl or ethyl group ;

R ² represents a hydrogen atom or a methyl or ethyl group ;

R ³ represents a hydrogen atom or a linear Ci_3 alkyl group ; and

each R ⁴ represents a hydrogen atom or a methyl or ethyl group; provided that both R ⁴ have in total, i.e. all together, 0, 1 or 2 carbon atoms ;

can be used as perfuming ingredient, for instance to impart odor notes of the white flower type- According to an embodiment of the invention, n is 1. Moreover, according to another embodiment of the invention, the dotted line represents a carbon-carbon single bond.

According to any one of the above embodiments of the invention, R ¹ represents a hydrogen atom or a methyl group.

According to any one of the above embodiments of the invention, R represents a hydrogen atom or a methyl group.

According to any one of the above embodiments of the invention, R ³ represents a a methyl, ethyl or n-propyl group, preferably a methyl or ethyl group.

According to any one of the above embodiments of the invention, each R ⁴ represents a hydrogen atom or a methyl group.

According to any one of the above embodiments of the invention, said compound (I) has an even total number of carbon atoms, in particular are Cio, C1 ₂ or C14, compounds. Moreover, in particular, when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C ₁₂ or C ₁₄ . In such a case the invention's compound has also the advantage of conferring also odor notes of the indol/naphthalene type.

Amongst the compounds responding to formula (I), the ones of formula

wherein n, the dotted line, R ¹ , R ² and R ⁴ have the meaning indicated in formula (I), and R ⁵ represents a hydrogen atom or a methyl or ethyl group;

are novel and therefore are also an object of the present invention.

According to an embodiment of formula (II), the invention's compound (II) has a even total number of carbon atoms, in particular are do, C ₁₂ or C ₁₄ , compounds. In particular, when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C ₁₂ or C ₁₄ .

For the sake of clarity, by the expression "wherein one dotted line represents a carbon-carbon single or double bond", or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the whole bonding (solid and dotted line) between the carbon atoms connected by said dotted line is a carbon-carbon single or double bond.

As specific examples of the invention's compounds, one may cite, as non-limiting example, 2-(l,2-dimethylbutyl)-cyclohexanol which possesses a jasmine/lily of the valley odor, with a very natural indole/naphthalene character. The overall odor is in between that of linalool (Arctander N° 1803) and that of indole (Arctander N° 1772). The odor of this compound is devoid of the herbaceous aspect of the rose or waxy/oily notes. This compound is quite interesting since it allies together the natural floral aspect of linalool and a well balanced indole/jasminic note, the latter having an animal character much less pronounced than the note of indole itself. As other example, one may cite 2-[(2E)-2-methyl-2-butenyl]cyclopentanol which possesses a floral, lilac/liUy of the valley type of odor with a bottom note of the indole, peppery type.

As other specific, but non-limiting, examples of the invention's compounds, one may cite the following ones in Table 1 :

Table 1 : Invention's compounds and their odor properties

According to a particular embodiment of the invention, the compounds of formula (I) are : 2-(l,2-dimethylbutyl)-cyclohexanol or 2-[(2E)-2-methyl-2- butenyl] cyclopentanol.

The odor of the invention's compounds, when compared with that of the prior art compounds, distinguishes itself by having a white flower character, as well as by lacking the herbaceous aspect of the rose or waxy/oily notes of the prior art compounds, despite the peculiar teaching of the prior art cited above. Said differences lend the invention's compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions. Moreover, the invention's compounds have the great advantage of allowing to impart indole type notes without the coloring problems typical of indole itself, and this even at very high concentrations.

As mentioned above, the invention concerns the use of a compound of formula (I) as perfuming ingredient. In other words, it concerns a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I). By "use of a compound of formula (I)" it has to be understood here also the use of any composition containing compound (I) and which can be advantageously employed in perfumery industry as active ingredients.

Said compositions, which in fact can be advantageously employed as perfuming ingredient, are also an object of the present invention.

Therefore, another object of the present invention is a perfuming composition comprising :

i) as perfuming ingredient, at least one invention's compound of formula (I), as defined above, provided that 2-(2-methylbutyl)-cyclohexanol or 2-(2-methylpropyl)- cyclohexanol and excluded ;

ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base ; and

iii) optionally at least one perfumery adjuvant.

According to a particular embodiment of the invention's perfuming composition, the perfuming ingredient is of formula (I), wherein R ¹ , R ² , R ³ and R ⁴ are as defined above, and when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C ₁₂ or C ₁₄ . Said perfuming ingredient, in particular, can be also a compound of formula (II).

By "perfumery carrier" we mean here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting example solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-l-ethanol or ethyl citrate, which are the most commonly used. For some applications, ethanol can also be commonly used as solvent.

As solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet encapsulating materials. Examples of such materials may comprise wall- forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloids : Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's VerlagGmbH & Co., Hamburg, 1996. The encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion ; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.

By "perfumery base" we mean here a composition comprising at least one perfuming co-ingredient.

Said perfuming co-ingredient is not of the formula (I). Moreover, by "perfuming co-ingredient" it is meant here a compound, which is used in perfuming preparation or composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.

The nature and type of the perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.

For the compositions which comprise both a perfumery carrier and a perfumery base, other suitable perfumery carrier, than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company).

By "perfumery adjuvant" we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.

An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.

It is useful to mention here that the possibility to have, in the compositions mentioned above, more than one compound of formula (I) is important as it enables the perfumer to prepare accords, perfumes, possessing the odor tonality of various compounds of the invention, creating thus new tools for their work.

For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture do not provide the inventive compound in a suitable form for perfumery. Unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.

Furthermore, the invention's compound can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, a perfumed consumer product comprising :

i) as perfuming ingredient, at least one compound of formula (I), as defined above; and ii) a fragrance good ;

is also an object of the present invention.

For the sake of clarity, it has to be mentioned that by "fragrance goods" we mean here a consumer product which is compatible with perfuming ingredients. In other words, a perfumed consumer product according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to a perfume compatible consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention's compound.

The nature and type of the constituents of the fragrance goods do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to the nature and the desired effect of said product.

Non-limiting examples of suitable fragrance goods can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, papers, or a bleaches ; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream or a deodorant or antiper spirant), or a skin-care product (e.g. a perfumed soap, shower or bath mousse, oils or gel, or an hygiene product); an air care product, such as a an air freshener or a "ready to use" powdered air freshener; or a home care product, such as a wipe, a dish detergent or hard-surface detergent.

Some of the above-mentioned consumer product bases may represent an aggressive medium for the invention's compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically bound it to another chemical which is suitable to release the invention ingredient upon a suitable external stimulus, such as an enzyme, light or a change of pH.

The proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as the nature of the co -ingredients in a given base when the compounds according to the invention are mixed with perfuming co- ingredients, solvents or additives commonly used in the art.

For example, in the case of perfuming compositions, typical concentrations are in the order of 0.1 % to 25 % by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.01 % to 15% by weight, can be used when these compounds are incorporated into perfumed articles, percentage being relative to the weight of the article.

The invention's compounds can be prepared according to a method a described in

(IV) (ΠΙ) (1) wherein n, the dotted line, R ¹ , R ² , R ³ and R ⁴ have the same meaning as indicated above.

Specific examples of reagent that can be used to promote each step of the above process are provided in the Examples herein below.

Alternatively, in the reaction Scheme above, instead of the ketone (IV) can be used a corresponding acetal, as also shown in the Examples.

Amongst the unsaturated ketones (III), the ones wherein R ³ represent a methyl, ethyl or n-propyl group, are novel and therefore are also an object of the present invention as intermediates for the compounds of formula (II) above described.

Examples

The invention will now be described in further detail by way of the following examples, wherein the abbreviations have the usual meaning in the art, the temperatures are indicated in degrees centigrade (°C) ; the NMR spectral data were recorded in CDCI ₃

(if not stated otherwise) with a 360 or 400 MHz machine for 1 H and 13 C, the chemical shifts δ are indicated in ppm with respect to TMS as standard, the coupling constants J are expressed in Hz.

Example 1

Synthesis of compounds of formula (I) a) 2-(l,2-dimethylbutyl)-cyclohexanol

2-[(2E)- 1 ,2-dimethyl-2-butenyl]cyclohexanone

Cyclohexanone dimethyl acetal (47.4 g; 0.33 mol), E-3-methyl-3-penten-2-ol (21.95 g; 0.22 mol), malonic acid (0.72 g; 0.007 mol) and BHT (50 mg) were heated together in a steel autoclave placed in an oil bath at 200°C for 48 hours. The product was then isolated by fractional distillation under high vacuum, using a 20-cm Widmer column. 23.83 g of the desired product were obtained (0.132 mol; yield: 60 %) as a 60:40 mixture of diastereoisomers.

B.p. = 110-115°C/0.02 mbar

'H-NMR: 5.35-5.15 (m, 1 H); 2.72-2.18 (m, 4 H); 1.92-1.70 (m, 4 H); 1.70-1.40 (m, 8

H); 0.95 (m, 3 H). 2-[(2E)- 1 ,2-dimethyl-2-butenyl]cyclohexanol

The ketone obtained in the previous step (5.00 g, 27.7 mmol) was dissolved in dry diethyl ether (10 ml) and added drop wise to a slurry of lithium aluminum hydride (1.32 g; 34.7 mmol) in dry diethyl ether (50 ml) under nitrogen, while cooling in an ice- water bath. After stirring for one more hour at 5°C, water (5 ml) was slowly added, followed by 5% aqueous sodium hydroxide (15 ml) and again water (5 ml). The mixture was warmed up to room temperature and stirred until a white slurry was obtained (15 minutes). Solid anhydrous sodium sulfate was added in order to dry the reaction mixture. The solid was filtered off, thoroughly rinsed with diethyl ether. The filtrate was concentrated on the rotavapor and the product purified by bulb-to-bulb distillation. 4.66 g of desired alcohol were obtained (25.5 mmol, yield: 92 %) as a mixture of diastereoisomers .

B.p. = 100 °C/1 mbar

'H-NMR: 5.40-5.20 (m, 1 H); 4.12-3.38 (m, 1 H); 2.40 1.80 (m, 2 H); 1.75-1.30 (m, 11

H); 1.70-0.90 (m, 7 H). 2-( 1 ,2-dimethylbutyl)cyclohexanol

The alcohol obtained in the previous step (1 g; 5.5 mmol) was dissolved in methanol (20 ml) and hydrogenated at room temperature and 20-40 bar of hydrogen in presence of 5 % palladium on carbon (0.15 g) for 18 hours. The catalyst was then filtered off, rinsed with methanol and the filtrate concentrated on the rotavapor. The product was purified by bulb-to-bulb distillation.

0.7 g of desired product were obtained (3.8 mol, yield: 69 %) as a mixture of diastereoisomers .

B.p. = 100 °C/1 mbar.

1H-NMR: 4.10-4.00 (m, 0.5 H); 3.60-3.38 (m, 0.5 H); 2.05-1.05 (m, 14 H); 1.05-0.65

(m, 9 H). b) 2-(l,2-dimethyl-2-propenyl)cyclohexanol

2-(l ,2-dimethyl-2-propenyl)cyclohexanone

Same procedure as for 2-[(2E)-l,2-dimethyl-2-butenyl]cyclohexanone : (see above a)), with the following reagents :

Cyclohexanone dimethyl acetal: 47.4 g; 0.33 mol

E-2-methyl-2-buten-l-ol: 18.9 g; 0.22 mmol;

Malonic acid: 0.72 g; 0.007 mol

BHT: 50 mg

24.39 g of desired product were obtained (0.147 mol; yield: 67 %) as a 57:43 mixture of diastereoisomers.

B.p = 34 °C/0.001 mbar

'H-NMR: 4.80-4.55 (m, 2 H); 2.77-2.57 (m, 1 H); 2.45-2.21 (m, 3 H); 1.98-1.47 (m, 9 H); 0.99 (m, 3 H). 2-( 1 ,2-dimethyl-2-propenyl)cyclohexanol

Same procedure as for 2-[(2E)-l,2-dimethyl-2-butenyl]cyclohexanol : (see above a)), with the following reagents : 2- (l ,2-dimethyl-2-propenyl)cyclohexanone: 10.0 g; 0.06 mol

Lithium aluminum hydride: 2.85 g; 0.075 mol

Diethyl ether (100 ml). 9.75 g of the desired alcohol were obtained (0.058 mol; yield: 96 %) as a mixture of diastereoisomers .

B.p. = 100 °C/3 mbar

'H-NMR: 4.85-4.65 (m, 2 H); 4.12-3.38 (m, 1 H); 2.55-1.35 (m, 11 H); 1.30-0.83 (m, 6 H). c) 2-[(2E)-2-methyl-2-butenyl]cyclopentanol

2- [(2E)-2-methyl-2-butenyl] cyclopentanone

Prepared as described for -[(2E)-l ,2-dimethyl-2-butenyl]cyclohexanone : (see above a)), with the following reagents : Cyclopentanone dimethyl acetal: 118 g; 0.88 mol

3- Methyl-3-buten-2-ol: 61.2 g; 0.71 mol

Malonic acid: 0.53 g; 0.005 mol

BHT: 50 mg 58.84 g of desired ketone were obtained (0.386 mol; yield: 54 %), as a 95:5 E/Z mixture B.p. = 63 °C/1.9 mbar

¹³ C-NMR (E-isomer): 221.36 (s); 133.45 (s); 120.31 (d); 47.65 (d); 39.88 (t); 38.18 (t);

29.30 (t); 20.59 (t); 15.40 (q) ; 13.40 (q).

'H-NMR (E-isomer) : 5.25-5.18 (m, 1 H) ; 2.50 (m, 1 H) ; 2.33-2.05 (m, 4 H); 2.02-1.93

(m, 1 H); 1.88- 1.70 (m, 2 H); 1.60 (s, 3 H); 1.55 (s, 3 H); 1.53- 1.45 (m, 1 H).

2- [(2E)-2-methyl-2-butenyl] cyclopentanol

Prepared as described for 2-[(2E)-l ,2-dimethyl-2-butenyl]cyclohexanol : (see above a)), with the following reagents :

2-[(2E)-2-methyl-2-butenyl]cyclopentanone : 20.08 g, 0.132 mol

Lithium aluminum hydride: 3 g, 0.075 mol

THF: 500 ml 19 g of the desired product were obtained (0.124 mol, yield: 94 %) as a 9:1 mixture of diastereoisomers .

B.p. = 89 °C/0.5 mbar

¹³ C-NMR (major isomer): 135.35 (s); 119.64 (d); 79.20 (d); 45.79 (d); 44.29 (t); 34.09

(t); 29.80 (t); 21.49 (t); 15.73 (q); 13.37 (q).

'H-NMR : 5.25 (m, 1 H) ; 3.81 (m, 1 H) ; 2.12-2.03 (m, 1 H) ; 1.97-1.78 (m, 5 H) ; 1.73- 1.50 (m, 3 H) ; 1.62 (s, 3 H) ; 1.58 (d, J = 7, 3 H) ; 1.22-1.12 (m, 1 H). d) 2-( l,2-dimethylpropyl)cyclopentanol

2-(l ,2-dimethyl-2-propenyl)cyclopentanone

Prepared as described for 2-[(2E)-l,2-dimethyl-2-butenyl]cyclohexanone : (see above a)), with the following reagents :

Cyclopentanone dimethyl acetal: 62 g, 0.48 mol

E-2-methyl-2-buten-l-ol: 32 g, 0.37 mol

Malonic acid: 0.3 g, 0.003 mol

BHT: 50 mg

34 g of desired product were obtained (0.224 mol, yield: 61 %) as a 1 : 1 mixture of diastereoisomers.

B.p. = 30-40 °C/0.01 mbar

'H-NMR: 4.80-4.70 (m, 2 H); 2.70 (m, 0.5 H); 2.43 (m, 0.5 H); 2.36-1.90 (m, 5 H);

1.80-1.55 (m, 2 H); 1.72 (s, 1.5 H); 1.61 (s, 1.5 H); 1.18 (d, J = 7; 1.5 H); 0.91 (d, J = 7; 1.5 H).

2-( 1 ,2-dimethylpropyl)cyclopentanone

The unsaturated ketone 2-(l,2-dimethyl-2-propenyl)cyclopentanone (14 g; 0.092 mol) was hydrogenated at room temperature and 30 bar hydrogen in cyclohexane (20 ml) in presence of 5 % palladium on carbon (0.3 g) for 5h30. The product was isolated by bulb-to-bulb distillation.

13.5 g of the desired ketone were obtained (0.087 mol; yield: 95 %) as a 1 :2 mixture of diastereoisomers .

B.p. = 99 °C/2 mbar

'H-NMR: 2.37-1.93 (m, 5 H); 1.90-1.65 (m, 3 H); 1.60-1.45 (m, 1 H); 0.97-0.70 (m, 9 H). 2-( 1 ,2-dimethylpropyl)cyclopentanol

Prepared as described for 2-[(2E)-l ,2-dimethyl-2-butenyl]cyclohexanol (see above a)), with the following reagents :

2-(l ,2-dimethylpropyl)cyclopentanone : 6.33 g; 0.041 mol

Lithium aluminum hydride: 1.64 g; 0.041 mol

THF: 100 ml. 5.9 g of the desired alcohol were obtained (0.038 mol; yield: 92 %) as a mixture of diastereoisomers .

B.p. = 95 °C/1 mbar

'H-NMR: 4.22-3.90 (m, 1 H); 2.00-1.50 (m, 8 H); 1.40-1.12 (m, 2 H); 0.92-0.72 (m, 9 H). e) 2-(2-methylbutyl)cyclopentanol

2-(2-methylbutyl)- 1 -cyclopentanone

Prepared as described for 2-(l ,2-dimethylpropyl)cyclopentanone (see above d)) with the following reagents : 2-[(2E)-2-methyl-2-butenyl]cyclopentanone : 19.8 g; 0.130 mol

5 % Pd-C: 0.3 g

Cyclohexane: 20 ml.

18.5 g of desired ketone were obtained (0.120 mol; yield: 92 %) as a 1 : 1 mixture of diastereoisomers.

B.p. = 90 °C/5 mbar

'H-NMR: 2.36-2.20 (m, 2 H); 2.17-1.96 (m, 3 H); 1.82-1.71 (m, 1 H); 1.60-1.03 (m, 6

H); 0.91-0.85 (m, 6 H). 2-(2-methylbutyl)cyclopentanol

Prepared as described for 2-[(2E)-l ,2-dimethyl-2-butenyl]cyclohexanol (see above a)), with the following reagents :

2-(2-methylbutyl)-l -cyclopentanone : 11.20 g; 0.073 mol

Lithium aluminum hydride: 2.9 g; 0.073 mol

THF: 250 ml. 10.3 g of the desired alcohol were obtained (0.066 mol; yield: 90 %) as mixture of diastereoisomers .

B.p. = 85 °C/0.48 mbar

^-NMR: 3.82-3.72 (m, 1 H); 1.96-1.50 (m, 8 H); 1.45-1.23 (m, 3 H); 1.21-0.96 (m, 2

H); 0.90-0.85 (m, 6 H). 2-(2 -ethyl- 1 -methyl-2-propenyl)-l -cyclohexanol

-(2-ethyl- 1 -methyl-2-propenyl)- 1 -cyclohexanone

Prepared as described for 2-[(2E)-l,2-dimethyl-2-butenyl]cyclohexanone : (see above a)), with the following reagents :

E-2-Ethyl-2-buten-l-ol (5 g; 0.05 mol)

Cyclohexanone dimethyl acetal (8 g; 0.055 mol)

Malonic acid: 30 mg

8.5 g of the desired ketone were obtained (0.047 mol; yield: 94 %) as a 16:84 mixture of diastereoisomers .

B.p. = 55 °C/0.3 mbar

'H-NMR: 4.80 (m, 2 H); 2.80-1.40 (m, 12 H); 1.00 (m, 6 H). -(2-ethyl- 1 -methyl-2-propenyl)- 1 -cyclohexanol

Prepared as described for 2-[(2E)-l,2-dimethyl-2-butenyl]cyclohexanol : (see above a)), with the following reagents :

2-(2-ethyl-l-methyl-2-propenyl)-l -cyclohexanone from previous step: 6.4 g; 0.01 LiAlH ₄ : 0.44 g; 0.011 mol

Diethyl ether: 50 ml 6.2 g of the desired alcohol were obtained (0.034 mol; yield: 96 %) as a 22: 16:61 mixture of diastereoisomers.

B.p. = 60 °C/0.3 mbar

'H-NMR: 4.80 (m, 2 H); 4.20-3.40 (m, 1 H); 2.10-1.00 (m, 19 H). Example 2

Preparation of a perfuming composition A perfuming composition, of the lilac type, was prepared by admixing the following ingredients :

Ingredient Parts by weight

Cinnamon alcohol 75

Anisic aldehyde 50

3-(4-tert-butylphenyl)-2-methylpropanal 100

Mayol ^{® l)} 35

Phenethylol 120

Terpineol 380

(2,2-dimethoxyethyl)benzene ²⁾ 40

800

1) cis-7-P-menthanol; origin: Firmenich SA, Geneva, Switzerland

2) origin: Firmenich SA, Geneva, Switzerland

The addition of 200 parts by weight of 2-(l,2-dimethylbutyl)-cyclohexanol to the above- described composition reinforced the floral, white floral/lilac of the letter composition. The effect obtained with the invention's compound was similar to the one achieved by adding 180 parts of linalool and 20 parts of indole, but the invention's compound did not impart an animal note. Moreover the composition with the invention's compound did not develop any coloring over time, while the composition containing linalool and indole strongly colored over time.

Example 3

A detergent's perfuming composition, of the flowery, woody and musky type, was prepared by admixing the following ingredients : Ingredient Parts by weight

Isobornyl acetate 30

Carbinol acetate 140

10%* Phenyl acetate 40

(Z)-3-hexen-l-ol acetate 10

Verdyl acetate 300

C 12 aldehyde 20

10%* Methyl benzoate 40

Benzylacetone 190

Citronellyl Nitrile 70

Coumarine 20

Allyl (cyclohexyloxy)-acetate 10

Allyl cyclohexylpropionate 20

Diphenyloxyde 60

2-Methyl-4-(2,2,3-trimethyl-3-cyclopenten- 1 -yl)-

4-penten-l-ol ^l) 90

2,4,6-Trimethyl-4-phenyl-l,3-dioxane ²⁾ 40

Habanolide ^{® 3)} 330

Hedione ^{® 4} ' 200

Allyl heptanoate 80

Ionone Alpha 50

Iralia ^{® 5)} Total 130

Iso E ^{® 6)} Super 220

Lihal ^{® 7)} 120

Lorysia ® 8) 300

10%* Methylacetophenone 20

Myroxyde ^{® 9)} 10

Rose oxide 30

Phenethylol 350

(2-Methoxyethyl)benzene 20

(Z)-3-hexen-l-ol 20 Orange essential oil

Verdyl propionate

Terpineol

Gamma undecalactone

Verdox ^{® 10)}

10%** Violettyne ^U)

Yara Yara

2,4-Dimethyl-3-cyclohexene- 1 -carbaldehyde

4400

* in dipropyleneglycol

** in isopropyle myristate

I) origin: Firmenich SA, Geneva, Switzerland

2) origin: Symrise AG, Germany

3) pentadecenolide; origin: Firmenich SA, Geneva, Switzerland

4) methyl cis-dihydrojasmonate; origin: Firmenich SA, Geneva, Switzerland

5) mixture of methylionones isomers; origin: Firmenich SA, Geneva, Switzerland

6) l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone; origin: International Flavors & Fragrances, USA

7) 3-(4-tert-butylphenyl)-2-methylpropanal; origin: Givaudan SA, Vernier, Switzerland

8) 4-(l ,l-dimethylethyl)-l-cyclohexyl acetate; origin: Firmenich SA, Geneva,

Switzerland

9) 6,7-epoxy-3,7-dimethyl-l,3-octadiene; origin: Firmenich SA, Geneva, Switzerland 10) 2-tert-butyl-l-cyclohexyl acetate; origin: International Flavors & Fragrances, USA

I I) l,3-undecadien-5-yne; origin: Firmenich SA, Geneva, Switzerland

The addition of 600 parts by weight of 2-(l,2-dimethylbutyl)-cyclohexanol to the above- described composition imparted to the letter a natural white flower, jaminic effect, having lots of volume and impact, with a much better balanced and subtle naphthalenic note than when indole was added instead of the invention's compound.