Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1989-08-07
1990-11-06
Lone, Werren B.
Perfume compositions
Perfume compositions
Ring containing active ingredient
512 25, 568715, 568814, A61K 446, C07C 3318
Patent
active
049686682
DESCRIPTION:
BRIEF SUMMARY
3-Phenylpropionaldehyde and 3-phenylpropan-1-ol have long been used as fragrances. Furthermore, the fragrant character of propionaldehydes of the general formula ##STR1## is disclosed in Japanese Published Specification JP 61,194,045 (CA 106:32752m).
The use of 1,1-di(C.sub.1 -C.sub.6 -alkyl)-2-phenylethane derivatives as perfumes is disclosed in European patent application No. 0 076,493. However, all compounds described therein exhibit no additional substitution of the phenyl radical, such as is evident, for example, for 2,2-dimethyl-3-phenylpropanol in Example 2 of this specification.
It has now been found that new fragrances having a predominantly floral character are formed by methyl substitution in the 3- or 3,5-position of the benzyl radical.
The invention relates to 2-methyl-3-(3-methylphenyl)-propan-1-ol, 2-methyl-3-(3,5-dimethylphenyl)propan-1-ol, 1-(3-methylphenyl)-2-methylbutan-3-ol and 1-3,5-dimethylphenyl)-2-methylbutan-3-ol.
A process for the preparation of 2-methyl-3-(3-methylphenyl)-propan-1-ol and 2-methyl-3-(3,5-dimethylphenyl)-propan-1-ol comprises propionaldehyde in the presence of bases and 3,5-dimethylbenzylmagnesium chloride with chloroacetone and base-catalyzed cyclization.
These reaction pathways are illustrated by the following reaction schemes. ##STR2##
The benzaldehydes, propionaldehyde, benzyl chlorides and chloroacetone used as starting compounds are known substances. The benzylmagnesium chlorides can be obtained in a manner known per se from metallic magnesium and the benzyl chlorides.
The reaction in accordance with (a) is preferably carried out using alkali metal hydroxides, in particular sodium hydroxide or potassium hydroxide, at temperatures of preferably -5.degree. C. to 80.degree. C. in polar solvents such as alcohols, for example methanol or ethanol. The reaction product in accordance with (a) is then hydrogenated using reduction catalysts such as palladium on active carbon or Raney nickel and hydrogen and the alcohol is finally separated by fractional distillation.
The reaction in accordance with (a1) is preferably carried out at temperatures from 0.degree. C. to 60.degree. C. in dry inert solvents such as diethyl ether and/or tetrahydrofuran with subsequent hydrolysis ideally in the presence of mineral acids such as hydrochloric acid, sulfuric acid and the like. The reaction product according to (a1) is subsequently cyclized to the epoxide using bases, preferably alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, at temperatures of preferably from 0.degree. C. to 50.degree. C., then catalytically hydrogenated, preferably using reduction catalysts such as palladium on active carbon and hydrogen and the alcohol is finally separated by fractional distillation.
A further process for the preparation of 2-methyl-3-(3-methylphenyl)-propan-1-ol and 2 -methyl-3-(3,5-dimethylphenyl)-propan-1-ol comprises diethyl methylmalonate, hydrolysis and 2-bromopropionate and, after elimination of water,
These reaction pathways are illustrated by the following reaction schemes. ##STR3##
Diethyl methylmalonate and methyl 2-bromopropionate are known compounds. The reaction in accordance with (a2) is preferably carried out at temperatures from 70.degree. to 120.degree. C. in the presence of a base such as sodium carbonate or potassium carbonate. After hydrolysis, for example using bases such as sodium hydroxide or potassium hydroxide, the product is thermally decarboxylated, preferably at 120.degree. C. to 150.degree. C. The acid obtained or the esterification product with alcohols such as methanol or ethanol is reacted with hydrogenating agents such as lithium aluminum hydride or hydrogen in the presence of a suitable catalyst.
The reaction in accordance with (a3) is preferably carried out at temperatures from 80.degree. C. to 110.degree. C. in the presence of metallic zinc. After elimination of water, the ester obtained is reacted with hydrogenating agents such as lithium aluminum hydride or hydrogen in the presence of a suitable catalyst.
Processes for the preparati
REFERENCES:
patent: 4490284 (1984-12-01), Brunke et al.
patent: 4549983 (1985-10-01), Wiegers et al.
patent: 4710316 (1987-12-01), Hafner et al.
Friedrich Wilhelm
Gebauer Walter
Hafner Walter
Markl Erich
Regiert Marlies
Consortium fur Elektrochemische Industrie GmbH
Lone Werren B.
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