1-(2,2,6-Trimethylcyclohexyl)- hexan-3-ol

Chemical properties

1-(2,2,6-Trimethylcyclohexyl)- hexan-3-ol is a colorless liquid with a highly diffusive, powdery, woody odor. It is amixture of the cis- and trans-isomers. The trans-isomer has a more distinct animal and amber character.
The title compound is prepared by condensation of citral with 2- pentanone in the presence of bases to give 8,12-dimethyltrideca-5,7,11-trien-4- one, which is cyclized and hydrogenated.
A high-trans mixture can be prepared starting from ??-cyclocitral, which is hydrogenated to 2,2,6-trimethylcyclohexane carboxaldehyde. Condensation with 2-pentanone in the presence of sodium ethoxide yields the corresponding 3-hexenone. Hydrogenation with nickel–copper chromite as a catalyst gives a mixture with up to 95% of the trans-isomer.
It is used in perfume compositions for soaps, detergents, and household products.

Trade name

Norlimbanol® (Firmenich), Timberol® (Symrise)