Composition essentially consisting of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol
AssigneeFirmenich SA
InventorsKarl-Heinrich Schulte-Elte, Gunther Ohloff, Bernard L. Muller, Wolfgang K. Giersch
Life of this patent
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Abstract
Composition consisting of from less than 100% to more than about 80% of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol and a definite amount, but not more than about 20%, of cis-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol. Process for preparing same from .beta.-cyclocitral via a three-, optionally, four-step pathway. Utilization of the said composition as effective perfume ingredient.
Claims12
A perfume composition comprising an odorous effective amount of an odorous composition containing from 50% to 100% of trans-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol- and not more than 50% of cis-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol.
A method for improving the odor of a perfume composition which comprises adding thereto an odorous effective amount of an odorous composition containing from 50% to 100% of trans-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol- and not more than 50% of cis-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol.
A perfumed article selected from the class of soaps, cosmetics, detergents, space odorants and deodorants comprising an odorous effective amount of an odorous composition containing from 50% to 100% of trans-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol and not more than 50% of cis-1-(2,6,6-trimethylcyclohexyl)hexan-3-ol.
A process for the preparation of essentially pure trans-1-(2,6,6-trimethylcyclohexyl)-3-hexan-3-ol which comprises the following sequentials steps:
- a. reducing .beta.-cyclocitral through hydrogenation with a supported palladium catalyst in alcohol at about ambient temperature and at about atmospheric pressure to form 1-formyl-2,6,6-trimethylcyclohexane,
- b. adding a predetermined amount of 2-pentanone to said 1-formyl-2,6,6-trimethylcyclohexane in the presence of a strong base to form a mixture containing a predominant amount, but not less than about 95% by weight of trans-1-(2,6,6-trimethylcyclohexyl)-hex-1-en-3-one and a predetermined amount, but not more than about 5% by weight, of cis-1-(2,6,6-trimethylcyclohexyl)-hex-1-en-3one,
- c. reducing the mixture thus obtained by contacting said mixture with an alkali metal aluminohydride at a pressure between slightly above atmospheric pressure and 100 atmospheres at a temperature between about 120.degree.-200.degree. C. in the presence of a catalytic amount of a Raney-nickel catalyst, said catalyst optionally including a predetermined amount of copper chromite and, optionally,
- d. separating the mixture thus obtained by preparative vapor phase chromotography to form an essentially pure trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol.
A cycloaliphatic ketone of formula ##STR14## wherein the wavy line stands for a C--C bond of cis or trans configuration with respect to the methyl group in position 2 of the ring.
A process for the preparation of essentially pure trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol, which comprises the following sequential steps:
- a. adding 2-pentanone to a predetermined volume of 1-formyl-2,6,6-trimethylcyclohexane in the presence of a strong base to form a mixture containing a predetermined amount, but not less than about 95% by weight, of trans-1-(2,6,6-trimethylcyclohexyl)-hex-1-en-3-one;
- b. reducing the mixture thus obtained by contacting said mixture with an alkali metal aluminohydride at a pressure between slightly above atmospheric pressure, and 100 atmospheres at a temperature between about 120.degree.-200.degree. C. in the presence of a catalytic amount of a Raney-nickel catalyst, said catalyst optionally including a predetermined amount of copper chromite and, optionally,
- c. separating the mixture thus obtained by preparative vapor phase chromotography to form an essentially pure trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol.
Dependencies are inferred from the claim text.