Enantiomerically pure alcohols are of tremendous importance in the pharmaceutical and agrochemical sectors. However, the preparation of enantiomerically pure alcohols is frequently very difficult, particularly when the processes for their preparation are to be suitable for a large-scale industrial reaction. Direct asymmetric synthesis is frequently possible only with considerable difficulty, if at all. An alternative route to enantiomerically pure alcohols is offered by resolution of racemates, which is classically carried out by crystallization of diastereomers or by means of kinetic racemate resolution. The great disadvantage of resolution of racemates is the fact that the yield is limited to a maximum of 50%. In addition, the crystallization method requires stoichiometric amounts of a chiral crystallization reagent to form the diastereomers. A further disadvantage of these processes is that the racemate resolution reagent usually has to be covalently bound to the alcohol, which makes such processes very complicated.

The dynamic kinetic resolution of racemates, which comprises a kinetic racemate resolution coupled with in-situ racemization (e. g. U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999 (10) 107), enables enantiomerically pure products to be obtained in yields above 50%. The enantiomers are in this case separated by means of a kinetic racemate resolution step, so that the direct synthesis of the enantiomeric product can also be dispensed with here.

In the preparation of enantiomerically pure alcohols, kinetic racemate resolution by enzymatic acylation is prior art; a review of this technique is given in R. Azerad et al.

Curr. Opinion Biotechnoi. 2000 (11) 565. A critical aspect of the dynamic kinetic resolution of racemic alcohols described there is appropriate choice of reaction conditions, since, in particular, the rapid racemization must not adversely affect the kinetic racemate resolution. Customary racemization methods for alcohols make use of strong bases or strong acids at elevated temperatures (E. J. Ebbers et al.

Tetrahedron 1997 (53) 9417). Under these conditions, racemate resolution in the presence of enzymes, for example, is not possible since mild reaction conditions are required for this.

A solution to this problem is offered by racemization of alcohols by means of homogeneous transition metal catalysts. A review of methods known for this purpose is given, for example, in R. Sturmer, Angew. Chem. Int. Ed. Engl. 1997 (36) 1173. A transition metal-catalyzed racemization of secondary alcohols is described, for example, in P. M. Dinh et al. Tetrahedron Lett. 1996 (42) 7623. In this process, various metals and additives are tested, and a few examples of enzymatic resolution of racemates are also described. However, the processes described give low yields and display low selectivities. An alternative process is described in J. H. Koh et al.

Tetrahedron Lett. 1998 (39) 5545, who carry out the dynamic kinetic resolution of racemates using commercially available ruthenium complexes and catalytic amounts of a strong base. This process likewise gives only low yields of enantiomerically pure alcohols. The same type of catalyst system is employed by J. H. Koh et al., Tetrahedron Letters 1999 (40) 6281, but using milder bases. This makes the use of enzymes in the syntheses described possible. However, this process requires stoichiometric amounts of oxygen. As a result, this process cannot be employed in industry, since a small amount of oxygen has to be metered in precisely under protective gas. In Angew. Chem. 1997 (109) 1256, and J. Am. Chem. Soc. 1999 <BR> <BR> (121) 1645, Backvall, J. -E. et al. describe an enzymatic dynamic kinetic resolution of racemic alcohols using ruthenium catalysts for the racemization. This enables enantiomeric alcohols to be obtained in high yields and with high selectivity. The critical disadvantage of this process is the high air-sensitivity of the catalyst. The ruthenium catalysts used have to be synthesized in a plurality of steps under protective gas, which rules them out for use on a large industrial scale.

It is therefore an object of the present invention to provide a process which allows alcohols to be racemized under mild conditions, so that combination of this with racemate resolution enables enantiomeric alcohols to be obtained with high selectivity and in a high yield.

Surprisingly, this object can be achieved by means of a mixture of ruthenium complexes with cheating N-donor ligands.

The present invention accordingly provides a process for the racemization of alcohols with addition of at least one ruthenium precursor and at least one cheating N-donor ligand. In this process, the ruthenium precursor can have been admixed beforehand with the cheating N-donor ligand to produce the catalytically active complex prior to the racemization. However, the catalytically active complex can also be formed in the racemization mixture in the presence of the alcohol, so that the racemization can be carried out in a single-vessel reaction.

As cheating N-donor ligands, use can be made of amines such as hydroxyamine or alkoxyamine compounds or diamines. Preference is given to ligands which form five- to twelve-membered chelate rings with the ruthenium; such a cheating ligand can be based on a C2-C10-alkyl, C3-C10-cycloalkyl, C2-C10-alkenyl or-alkynyl, C5-C8- cycloalkenyl, phenyl, naphthyl, fluorenyl or C5-C14-aryl skeleton, in each of which one or two carbon atoms may be replaced by heteroatoms from the group consisting of N, O and S.

The basic skeleton may bear, in addition to hydrogen, further substituents selected from the group consisting of C1-C10-alkyl, C2-C10-alkenyl and -alkynyl, C5-C14-aryl, C1-C10-alkoxy, C-Co-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C8-aryl, phenyl, naphthyl, fluorenyl, C2-Cg-heteroalkyl, C-Cg-heteroalkenyl, C2-C6-heteroaryl, where the number of heteroatoms from the group consisting of N, O and S can be from 1 to 4, C1-Cg-trihalomethylalkyl, O-aryl-(C6-C10), OCO-alkyl-(C1-C8), OCO-aryl- (C6-C10), 0-phenyl, OH, NO2, COOH, S03H, NH-alkyl-(C1-C8), NH-aryl, N-alkyl2-(C1- C8), N-aryl2, SO2-alkyl-(C1-C6), SO2-aryl-(C6-C10), SO-alkyl-(C1-C6), NHCO-alkyl-(C1- C4), COO-alkyl-(C1-C8), COOaryl-(C6-C10), CONH2, CO-alkyl-(C1-C8), CO-aryl, NHCOH, NHCOO-alkyl-(C1-C4), CO-phenyl, COO-phenyl, CHCH-CO2-alkyl-(C1-C8), PO-phenyl2, POalkyl2-(C1-C4), PO3H2, PO (O-alkyl-(C1-C6)) 2, SO3-alkyl-(C1-C4), trifluoromethyl, trichloromethyl, fluoro, chloro, bromo, iodo, cyano and tri- (CI-C6)- alkylsilyl.

Preference is given to cheating diamine ligands of the formula (I), R'RN- (CR2) n-NR3R4 Formula (I) where n can be an integer from 2 to 9 and each of the up to 18 substituents R in formula (I) can be, independently of one another, hydrogen, (C1-C10)-alkyl or (C5-C10)-aryl and R1 to R4 are each, independently of one another, substituents selected from the group consisting of hydrogen, (C1-C10)-alkyl and (C5-C10)-aryl.

In a preferred embodiment, n is two, three or four. R is particularly preferably hydrogen and R1 to R4 are each, independently of one another, particularly preferably a (C1-C4)-alkyl radical, in particular a methyl radical.

Particular preference is given to ligands selected from the group consisting of N, N, N', N'-tetraethylethylenediamine, N, N, N', N'-tetraethyl-1, 3-propanediamine, N, N, N', N'-tetraethyldiethylenetriamine, N, N, N', N'-tetramethyl-1, 3-butanediamine, N, N, N', N', N"-pentamethyldiethylenetriamine, N, N, N'-trimethyl-1, 3-propanediamine, N, N, N', N'-tetramethyl-1, 6-hexanediamine, N, N, N', N'-tetramethyl-1, 4-butanediamine, N, N, N', N'-tetramethyl-1, 3-propanediamine, N, N, N', N'-tetraisopropylethylenediamine, N, N, N', N'-tetraisopropylethylenediamine and N, N, N', N'-tetrabutyl-1, 6- hexanediamine. Very particular preference is given to using N, N, N', N'- tetramethylethylenediamine or N, N, N', N'-tetramethyl-1, 3-propanediamine as ligand for the process of the invention.

Examples of suitable hydroxyamine compounds are 2-methoxybenzylamine and 4-hydroxy-4-phenylpiperidine. However, it is also possible to use ligands which together with the ruthenium form a chelate ring which contains one or two further heteroatoms from the group consisting of N, O and S. An example of such a ligand is N, N, N', N'-tetramethyidipropylenetriamine.

The efficiency of the racemization increases with increasing amounts of ligand used, based on the substrate. The molar ratio of ligand to ruthenium precursor is advantageously from 1: 1 to 200: 1, with the optimum molar ratio for each ligand, in particular in combination with the respective ruthenium precursor and the respective substrate, being able to be determined in a simple manner. Thus, for example, when N, N, N', N'-tetramethyl-1, 3-propanediamine is used as ligand, a molar ratio to the di-p- chlorobis [p-cymene] chlororuthenium (lI) precursor of 10: 1 is sufficient to achieve virtually complete racemization of (+)-1-phenylethanol in a short time.

As ruthenium precursor, it is possible to use, for example, carbonyl- tris (triphenylphosphine) dihydridoruthenium (li), ruthenium (II) acetylacetonate, dodecacarbonyltriruthenium, ruthenium (II) chloride hydrate, chloro (cyclopentadienyl) bis (triphenylphosphine) ruthenium, dichlorodicarbonylbis (triphenylphosphine) ruthenium (II), tris (triphenylphosphine) ruthenium (ll) chloride, ruthenium on activated carbon, chloro (indenyl) bis (triphenylphosphine) ruthenium (li), cis-dichlorobis (2, 2'- bipyridine) ruthenium (II) dihydrate or dichloro [ (S)- (-)-2, 2'-bis (diphenylphosphino)- 2, 2'-binaphthyl] ruthenium (II).

Particular preference is given to using di-p-chlorobis [p-cymene] chlororuthenium (II) or benzeneruthenium (li) chloride dimer.

Organic solvents are suitable as solvents. Thus, for example, esters, ethers, tertiary alcohols or aliphatic or aromatic hydrocarbons allow good racemization to be achieved. Diethylene glycol dimethyl ether, xylene and toluene, in particular, also give very good yields. N, N-Dimethylacetamide, ethylene glycol, 1,4-dioxane, 1-methyl-2-pyrrolidone and dimethylformamide likewise give high yields, but the racemization is less successful.

In addition, further additives can be added to the reaction mixture. The most important additives which come into question are bases, acids and/or ketones. A preferred additive is the ketone corresponding to the alcohol to be racemized.

The racemization of alcohols using cheating N-donor ligands is not subject to any restrictions in respect of the alcohol substrate.

Suitable substrates are, for example, secondary alcohols of the formula R'-CHOH- R", where the radicals R'and R"can each be, independently of one another, an alkyl-(C1-C20), cycloalkyl-(C3-C20), heterocycloalkyl-(C3-C20), alkenyl-(C2-C20),<BR> alkynyl-(C2-C20), aryl-(C5-20), heteroaryl-(C3-20), cycloalkenyl-(C5-C20), phenyl, naphthyl or fluorenyl group, where the number of heteroatoms selected from the group consisting of N, O and S can be from 1 to 4, and the radicals R'and R"may bear further substituents selected from the group consisting of C1-C10-alkyl, C2-C10- alkenyl and-alkynyl, C5-C14-aryl, C1-C10-alkoxy, C-Co-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C8-aryl, phenyl, naphthyl, fluorenyl, C2-Cs-heteroalkyl, C1-Cs- heteroalkenyl and C2-C6-heteroaryl, where the number of heteroatoms from the group consisting of N, O and S can be from one to four, C-Cg-trihalomethylalkyl, O- aryl-(C6-C10), OCO-alkyl-(C1-C8), OCO-aryl-(C6-C10), O-phenyl, OH, NO2, COOH, S03H, NH-alkyl-(C1-C8), NH-aryl, N-alkyl2-(C1-C8), N-aryl2, SO2-alkyl-(C1-C6), SO2- aryl-(C6-C10), SO-alkyl-(C1-C6), NHCO-alkyl-(C1-C4), COO-alkyl-(C1-C8), COOaryl- (C6-C10), CONH2, CO-alkyl-(C1-C8), CO-aryl, NHCOH, NHCOO-alkyl- (C,-C4), Co- phenyl, COO-phenyl, CHCH-CO2-alkyl-(C1-C8), PO-phenyl2, POalkyl2-(C1-C4), PO3H2, PO (O-alkyl- (CI-C6)) 2, SO3-alkyl-(C1-C4), trifluoromethyl, trichloromethyl, fluoro, chloro, bromo, iodo, cyano and tri-(C1-C6)-alkylsilyl.

Preferred alkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl and alkynyl groups contain up to 10 carbon atoms, particularly preferably up to 3 carbon atoms.

Preferred aryl and heteroaryl groups contain up to 10 carbon atoms, particularly preferably from 5 to 7 carbon atoms. In the groups containing heteroatoms, preference is given to one or two carbon atoms being replaced by one or two nitrogen atoms or one carbon atom being replaced by an oxygen or sulfur atom.

Particularly preferred alcohol substrates are secondary alcohols of the formulae (C5- Clo)-aryl-CHOH-alkyl- (Cl-Clo), phenyl-CHOH-R"and naphthyl-CHOH-R".

The present invention further provides a process for dynamic kinetic resolution of racemates which comprises a racemization step according to the invention. In particular, the racemization described is combined with an enzymatic racemate resolution, e. g. by addition of a hydrolase in the presence of an acyl donor.

In this process, enantiomeric alcohols having an enantiomeric excess (ee) of over 90% can be prepared in good yields in a"single-vessel"reaction without recourse having to be made to a technically complicated process or catalysts which are complicated to prepare.

The present invention further provides for the use of ruthenium complexes comprising at least one cheating N-donor ligand or a mixture comprising at least one ruthenium precursor and at least one cheating N-donor ligand for the racemization or dynamic kinetic racemate resolution of secondary alcohols.

Examples : Examples 1 to 23: Racemization of (+)-1-phenylethanol with variation of the ligand and the ligand concentration In a Schlenk tube, 15 mg (0.025 mmol) of di-, u-chlorobis [(p-cymene) chloro- ruthenium (ll)] are suspended in 2.5 ml of dry toluene at room temperature under protective gas and admixed with various ligands (see table 1) and different amounts of ligand (see table 2).

After about 10 minutes, 0.8 mmol of (+)-1-phenylethanol is added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 ul of hexadecane).

Table 1: Variation of the ligand Example Ligand (0. 25mmol) Yield ee % % 1 None 98 99 2 N, N,N',N'-Tetramethylethylenediamine 88 40 3 N, N, N', N'-Tetraethylethylenediamine 93 65 4 N, N, N', N'-Tetraethyl-1, 3-propanediamine 85 39 5 N, N, N', N'-Tetraethyldiethylenetriamine 92 71 6 N, N, N', N'-Tetramethyl-1, 3-butanediamine 88 41 7 N, N, N', N', N"-Pentamethyldiethylenetriamine 83 23 8 N, N, N', N'-Tetramethyldipropylenetriamine 86 20 9 N, N, N'-Trimethyl-1, 3-propanediamine 88 31 10 N, N, N', N'-Tetramethyl-1, 6-hexanediamine 85 33 11 N, N, N', N'-Tetramethyl-1, 4-butanediamine 87 35 12 N, N, N', N'-Tetramethyl-1, 3-propanediamine 85 1 13 2-Methoxybenzylamine 90 72 14 4-Hydroxy-4-phenylpiperidine 96 88 15 N, N, N', N'-Tetraisopropylethylenediamine 94 82 16 N, N, N', N'-Tetraisopropylethylenediamine 98 75 17 N, N, N', N'-Tetrabutyl-1, 6-hexanediamine 97 68 Table 2: Variation of the amount of ligand Example Ligand (amount of ligand) Yield ee % % 18 N, N, N', N'-Tetramethylethylenediamine (0.1 mmol) 84 30 19 N, N, N', N'-Tetramethylethylenediamine (0.15 mmol) 85 33 20 N, N, N', N'-Tetramethylethylenediamine (0.5 mmol) 80 19 21 N, N, N', N'-Tetramethyl-1, 3-propanediamine 86 9 (0.1 mmol) 22 N, N, N', N'-Tetramethyl-1, 3-propanediamine 85 1 (0.25 mmol) 23 N, N, N', N'-Tetramethyl-1, 3-propanediamine 83 0. 1 (0.5 mmol) Examples 24 and 25: Racemization of (+)-1-phenylethanol with addition of acetophenone The reactions were carried out in a manner analogous to examples 1 to 23 with addition of 0.4 mmol of acetophenone as additive.

Table 3: Reactions with additional acetophenone Example Ligand (amount of ligand) Yield ee % % 24 N, N, N', N'-Tetramethylethylenediamine (0.1 mmol) 93 13 25 N, N, N', N'-Tetramethyl-1, 3-propanediamine 85 33 (0.1 mmol) Examples 26 to 37: Racemization of (+)-1-phenylethanol In a Schlenk tube, 15 mg of a metal precursor (table 4) are suspended in 2.5 mi of dry toluene at room temperature under protective gas and admixed with 0.25 mmol of N, N, N'N'-tetramethylethylenediamine.

After about 10 minutes, 0.8 mmol of (+)-1-phenylethanol is added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 ul of hexadecane).

Table 4: Variation of the metal precursors used Example Metal precursor Yield ee % % 26 None 99 100 27 Di-p-chlorobis [p-cymene] chlororuthenium (ll) 88 30 (0.025 mmol) 28 Dodecacarbonyltriruthenium (0.025 mmol) 98 97 29 Ruthenium (II) chloride hydrate (0.025 mmol) 99 81 30 Chloro (cyclopentadienyl) bis (triphenylphosphine) 99 86 ruthenium (0.025 mmol) 31 Dichlorodicarbonylbis (triphenylphosphine) ruthenium (II) 99 94 (0.025 mmol) 32 Ruthenium 5% on activated carbon (50 mg) 98 96 33 Chloro (indenyl) bis (triphenylphosphine) ruthenium (i 1) 98 31 (0.025 mmol) 34 Tris (triphenyl phosphine) ruthenium (II) chloride 97 93 (0.025 mmol) 35 Cis-Dichlorobis (2, 2'-bipyridine) ruthenium (II) dihydrate 99 96 (0.025 mmol) 36 Dichloro [ (S)- (-)-2, 2'-bisdiphenylphosphino)-2, 2'- 94 92 binaphthyl] ruthenium (II) (0.025 mmol) 37 Benzeneruthenium (I I) chloride dimer (0. 025 mmol) 89 56 Examples 38 to 49: Racemization of (+)-1-phenylethanol In a Schlenk tube, 15 mg (0.025 mmol) of di-, u-chlorobis [(p-cymene) chloro- ruthenium (ll)] are suspended in 2.5 ml of dry solvent (table 5) at room temperature under protective gas and admixed with 0.25 mmol of N, N, N', N'-tetramethyl-1, 3- propanediamine.

After about 10 minutes, 0.8 mmol of (+)-1-phenylethanol is added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 ut of hexadecane).

Table 5: Variation of the solvent used Example Solvent Yield ee % % 38 Toluene 85 0. 5 39 Tert-butyl acetate 59 16 40 Tert-butanol 73 41 Xylene 82 13 42 Diethylene glycol dimethyl ether 91 1 43 N, N-Dimethylacetamide 90 59 44 Cyclohexane 69 30 45 Ethylene glycol 98 86 46 Dimethylformamide 89 35 47 Acetonitrile 71 43 48 1, 4-Dioxane 89 56 49 1-Methyl-2-pyrrolidone 99 61 Examples 50 to 59: Racemization of (+)-1-phenylethanol In a Schlenk tube, 15 mg (0.025 mmol) of di-p-chlorobis [ (p-cymene) chloro- ruthenium (ll)] are suspended in 2.5 ml of dry toluene at room temperature under protective gas and admixed with 0.25 mmol of N, N, N', N'- tetramethylethylenediamine.

After about 10 minutes, 0.8 mmol of (+)-1-phenylethanol and an additive (table 6) are added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 pi of hexadecane).

Table 6: Variation of the additives Example Additive Yield ee % % 50 None 87 28 51 Sodium acetate (0.1 mmol) 81 55 52 KOH (0.05 mmol) 78 2 53 LiBr (0.05 mmol) 89 46 54 p-Toluenesulfonic acid (0.05 mmol) 87 17 55 p-Toluenesulfonic acid (0.025 mmol) 88 47 56 p-Chlorophenol (0.05 mmol) 86 38 57 Triethylamine (0.05 mmol) 86 38 58 Tetraethylammonium bromide (0.05 mmol) 86 41 59 Tetrabutylammonium iodide (0.05 mmol) 78 53 Examples 60 to 65: Racemization of various secondary alcohols with addition of N, N, N', N'-tetramethyl-1, 3-propanediamine In a Schlenk tube, 15 mg (0.025 mmol) of di-, u-chlorobis [(p-cymene) chloro- ruthenium (ll)] are suspended in 2.5 ml of dry toluene at room temperature under protective gas and admixed with 0.25 mmol of N, N, N', N'-tetramethyl-1, 3- propanediamine.

After about 10 minutes, 0.8 mmol of an enantiomerically pure secondary alcohol (table 7) is added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 pl of hexadecane).

Table 7: Racemization of various secondary alcohols Example Secondary alcohol Yield ee % % 60 (+)-R-1-Phenyl-1-propanol 94 62 61 (+)-R-1-Indanol 90 0, 1 62 (-)-S-Methyl-2-naphthylmethanol 91 20 63 (-)-R-2-Octanol 70 70 64 (+)-R-4-Methoxy-1-phenylethanol 90 8 65 (+)-R-1-Phenylethanol 85 0, 5 Examples 66 to 71: Racemization of various secondary alcohols with addition of N, N, N', N'-tetramethyl-1, 2-ethylenediamine In a Schlenk tube, 15 mg (0.025 mmol) of di-, u-chlorobis [(p-cymene) chloro- ruthenium (II)] are suspended in 2.5 ml of dry toluene at room temperature under protective gas and admixed with 0.25 mmol of N, N, N', N'-tetramethyl-1, 2- ethylenediamine.

After about 10 minutes, 0.8 mmol of an enantiomerically pure secondary alcohol (table 8) is added and the mixture is stirred at 80°C for 5 hours. The yields and enantiomeric excesses (ee) are determined by means of gas-chromatographic analysis (internal standard: 100 iul of hexadecane).

Table 8 : Racemization of further secondary alcohols Example Secondary alcohols Yield ee % % 66 (+)-R-1-Phenyl-1-propanol 90 80 67 (+)-R-1-Indanol 89 3 68 (-)-S-Methyl-2-naphthylmethanol 88 85 69 (-)-R-2-Octanol 69 82 70 (+)-R-4-Methoxy-1-phenylethanol 88 20 71 (+)-R-1-Phenylethanol 79 30 Examples 72 to 79: Dynamic kinetic racemate resolution of secondary alcohols In a Schlenk tube, 15 mg (0.025 mmol) of di-p-chlorobis [(p-cymene) chloro- ruthenium (ll)] are suspended in 2.5 ml of dry toluene at room temperature under protective gas and admixed with 0.25 mmol of N, N, N', N'-tetramethyl-1, 3- propanediamine.

After about 10 minutes, 0.8 mmol of a racemic secondary alcohol (table 9), if applicable 0.4 mmol of an additive (table 9), 1.8 mmol of p-chlorophenyl acetate and 60 mg of Chirazym 1-2, c-f, lyo are added and the mixture is stirred at 80°C for 45 hours. The yields and enantiomeric excesses (ee) are determined by means of gas- chromatographic analysis (internal standard: 100 u of hexadecane).

Table 9: Dynamic kinetic racemate resolution of secondary alcohols Ex. () secondary Additive (0.4 mol) Yield of R-Product alcohol (0.8 mol) acetate in % ee in % 72 1-I ndanol 72 98 73 1-I ndanol 1-I ndanone 93 98 74 Methyl-2-58 98 naphthylmethanol 75 Methyl-2-Acetophenone 64 96 Naphthylmethanol 76 4-Methoxy-1-59 93 Phenylethanol 77 4-Methoxy-1-4-Methoxyacetophenone 66 97 Phenylethanol 78 1-Phenylethanol 72 96 79 1-Phenylethanol Acetophenone 80 98