Branched chain olefinic alcohols, thiols, esters and ethers, organoleptic uses thereof, processes for preparing same and intermediates therefor

A composition of matter comprising a major proportion of compounds characterized according to the structure:

• ##STR179## wherein in each of the molecules of the mixture one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represents a carbon-carbon single bond, said composition of matter produced according to the process comprising the steps of:
• (a) dimerization of isoamylene in the presence of an acid catalyst to form a mixture of diisoamylene compounds defined according to the structure:
• ##STR180## wherein R.sub.1 ", R.sub.2 ", R.sub.3 ", R.sub.4 " and R.sub.5 " represents hydrogen or methyl with three of R.sub.1 ", R.sub.2 ", R.sub.3 ", R.sub.4 " and R.sub.5 " representing methyl and the other two of R.sub.1 ", R.sub.2 ", R.sub.3 ", R.sub.4 " and R.sub.5 " representing hydrogen;
• (b) reacting the resulting diisoamylene mixture with a compound selected from the group consisting of acetyl chloride and acetic anhydride in the presence of an acid catalyst to form a mixture containing a major proportion of compounds defined according to the structure:
• ##STR181## wherein in each of the molecules, one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds;
• (c) reacting the resulting compound with methyl lithium at a temperature in the range of from 25.degree. C. up to 50.degree. C. in the presence of an inert solvent thereby forming a mixture of organolithium salts;
• and
• (d) reacting the resulting mixture of organolithium salts with dilute aqueous mineral acid at a temperature of from 0.degree. C. up to about 50.degree. C. thereby forming a mixture of compounds containing a major proportion of compounds having the structure:
• ##STR182## wherein in each of the molecules, one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds;
• and
• (e) distilling the resulting mixture.