Preparation of unsaturated alcohols
AssigneeTexas Alkyls, Inc.
InventorsSpencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
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Abstract
This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominately cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
Claims8
A process of preparing a predominately cis-unsaturated alcohol having the following formula:
- ##STR4## wherein R.sub.1 is a straight or branched chain alkyl group having 1 to 16 carbon atoms, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 can be the same or different and are selected from hydrogen, a straight or branched chain alkyl group having 1 to 12 carbon atoms, an aryl radical having 6 to 10 carbon atoms, said aryl radical can be substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy radical having 1 to 6 carbon atoms and halogen;
- comprising the steps of:
- a. pre-coordinating a predominately cis-1-alkenyl aluminum dialkyl compound having the following formula:
- ##STR5## wherein R can be selected from lower alkyl having 1 to 6 carbon atoms and R.sub.1 has been previously defined;
- with at least one molar equivalent of a Lewis base,
- b. reacting said product of step (a) with an epoxide compound having the following formula:
- ##STR6## wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have been previously defined, said reaction being carried out at a temperature of between -80.degree. C. and 130.degree. C.;
- c. treating the reaction product of steps (a) and (b) with an aqueous solution of a mineral acid, to yield the cis-unsaturated alcohol compounds.
Dependencies are inferred from the claim text.