Summary of the Invention In one aspect the invention provides 2- (cyclododecadienyl)-1-propan-1-ol.

For brevity and simplicity, this material will be referred to herein as"the compound","the novel compound"or"the compound of the invention".

The novel compound has the structure shown in Figure 1, in which one double bond may have E-or Z-geometry, the remaining double bond being E-.

The compound can be produced by reaction of 2- (cyclododecadienyl) propan-1-al, which is one of the products of Lewis acid-catalysed reaction of 1,5,9-cyclododecatriene with propylene oxide, e. g. using AICI3 as catalyst. The principal product of this reaction is 2- (4,8-cyclododecadienyl) propan-1-al. Reduction is conveniently effected using sodium borohydride, with the principal product being 2- (4, 8-cyclododecadienyl)-1-propan-1-ol. The Meerwein-Ponndorf reaction may alternatively be used.

In a further aspect the invention provides a method of making the compound of the invention, comprising reducing 2- (cyclododecadienyl) propan-1-al.

The compound of the invention exhibits an odour of amber, and so may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume. For the purposes of this invention a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensable or desirable. Examples of such products are: fabric washing powders, washing liquids, fabric softeners and other

fabric care products; detergents and household cieaning, scouring and disinfection products; air fresheners, room sprays and pomanders; soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products; cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc.

Other fragrance materials which can be advantageously combined with the compound according to the invention in a perfume are, for example, natural products such as extracts, essential oiis, absolutes, resinoids, resins, concretes etc., but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.

Such fragrance materials are mentioned, for example, in S. Arctander,"Perfume and Flavor Chemicals" (Montclair, N. J., 1969), in S. Arctander,"Perfume and Flavor Materials of Natural Origin" (Elizabeth, N. J., 1960) and in"Flavor and Fragrance Materials-1991", Allured Publishing Co. Wheaton, III. USA.

Examples of fragrance materials which can be used in combination with the compound according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, a-hexylcinnamaldehyde, 2-methyl-3- (p-tert-butylphenyl) propanal, 2-methyl-3- (p-isopropylphenyl) propanal, 3- (p-tert-butylphenyl)-propanal, 2,4-dimethylcyclohex-3-enyl- carboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4- (4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 4- (4-methyl-3-pentenyl)-3- cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-2- cyclopentenone, n-decanal, n-dodecanal, 9-decenol-1, phenoxyethyl isobutyrate, phenylacetaidehyde dimethylacetal, phenylacetaldehyde diethylacetal, geranyl nitrile, citronellyl nitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropin, coumarin, eugenol, vanillin,

diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylionones, irones, cis-3-hexenol and esters thereof, indan musks, tetralin musks, isochroman musks, macrocyclic ketones, macrolactone musks, ethylene brassylate.

Solvents which can be used for perfumes which contain the compound according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.

The quantities in which the compound according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the compound is used and on the olfactive effect desired. It is therefore only possible to specify wide limits, which, however, provide sufficient information for the specialist in the art to be able to use the compound according to the invention for his specific purpose. In perfumes an amount of 0.01% by weight or more of the compound according to the invention will generally have a clearly perceptible olfactive effect.

Preferably the amount is 0.1 to 80% by weight, more preferably at least 1%. The amount of the compound according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm. However, levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed.

In a further aspect the invention thus provides a perfume comprising the compound of the invention in an olfactively effective amount.

The invention also covers a perfumed product comprising the compound of the invention.

The invention will be further described, by way of illustration, in the following Example and with reference to the accompanying figures, in which: Figure 1 shows the structure of 2- (cyclododecadienyl) propan-1-ol; and Figure 2 shows the major products of Lewis acid-catalysed reaction of 1,5,9-cyclododecatriene with propylene oxide, and subsequent conversion of 2- (cyclododecadienyl) propan-1-al to the compound of the invention.

Example (a) Lewis Acid-Catalysed Reaction of 1,5,9-Cyclododecatriene with Propylene Oxide 1,5,9-cyclododecatriene (150 g; 0.924 mol) and propylene oxide (69 g; 1.2 mol) were mixed together, and added, with stirring, to a suspension of AIC13 (129 g; 0.96 mol) in CH2CI2 (750 ml) at-50° C. The reaction mixture was allowed to reach ambient temperature, then was added to a mixture of ice (4000 ml) and diethyl ether (2000 ml). The ether layer was separated and dried over MgS04. Chromatography (silica; hexane) gave recovered 1,5,9-cyclododecatriene (51.2 g). Further elution, using a mixture of hexane (90%) and diethyl ether (10%) as eluent gave a pale yellow oil (27.2 g), which was identified as 2-(cyclododecadienyl) propan-1-al.(cyclododecadienyl) propan-1-al. M+220. Kovats 1755,1773,1775,1781.

'H NMR (CDCI3) Signal Multiplicity Area Assignment 9.78 d 1 CHO 9.71 d 5.60-5.12 m 4 CH=CH 2.53-1.12 m 16 CH2 and CH 1.10 d 3 CH3 0.94 d The main products of the reaction of 1,5,9-cyclododecatriene (1) are shown in Figure 2.

These are 2- (cyclododecadienyl) propan-1-al (2) (15-22% conversion, based on recovered cyclododecatriene), 2-methyl-2,3,3a, 4,5,8,9,12,13,13a-decahydrocyclododeca [b] furan (3) (5% conversion), and a complex mixture of isomeric (M+220) and higher molecular weight alcools (40-55% conversion), from which the tricyclic propan-2-ol (4) was isolated.

(b) Reduction of 2- (Cyclododecadienyl) propan-1-al to 2- (Cyclododecadienyl) propan-1-ol 2- (Cyclododecadienyl) propan-1-al (4 g; 0.018 mol), obtained as above, dissolved in ethanol (10 ml), was added dropwise to a suspension of NaBH4 (1.0 g; 0.026 mol) in ethanol (80 ml). After complete addition, the reaction mixture was allowed to stir for 1 hour, then most

ethanol was removed in vacuo. CH2CI2 (150 ml) was then added, and the reaction mixture stirred while adding 2N HCI (aq) dropwise, until effervescence ceased. The organic layer was separated, washed, and dried over MgSO,. Chromatography (silica; hexane 50%, diethyl ether 50%) gave a colourless oil (3.3 g, 81%), identified as 2- (cyclododecadienyl) propan-1-ol ( (5) in Figure 2). A sample (2 g) was short-path distilled, b. p. 115° C at 1 mbar. M+222. The material consists of five isomers.

Kovats Area 1822 21.2% 1836 14.0% 1839 9.4% 1845 22.5% 1854 29.1% Total: 96.2% 'H NMR (CDCI3) Signal Multiplicity Area Assignment 5.50-5.08 m 4 CH=CH AB complex 2 CH2OH 2.20 s 1 OH 2.38-1. 02 m 16 ring CH2 + CHCH (CH3) OH 1.00-0.79 t overlapping 3 CH3 '3C NMR (CDCI3) 132.603,132.567,132.384,132.311,132.238,132.064,131.972, 131.680,131.657,131.570,131.524,131.360,131.214,129.650, 129.558,129.357,129.101,128.955,128.726,128.397 (all CH=CH) 67.407,65.803,65.201,64.003,63.900 (all CH2OH) 37.268,36.317,36.107,35.220,34.781 (all CH) 313,28.581,27.914,27.146, 26.213,25.317,24.594,23.781,22.638 (all CH2) 15.990,15.505,14.966 (CH) 10.952,10.549 (CH3) Catalytic hydrogenation of the compound of the invention produces 2-cyclododecylpropan-1-ol, which is a known substance exhibiting an intense and tenacious amber character.