Shell Oil Comapny

Aaldert J De Jong

Robin T Gray

Albertus J Mulder

Hendrik Schadenberg

Hendricus J Heijmen

Corrie M Leenaars

Novel cyclohexane derivatives of the formula: ##STR1## wherein R.sup.1 represents an alkyl group, R.sup.2 and R .sup.3 each represents a hydrogen atom or an alkyl group, and X represents an epoxy or hydroxy group; are useful as aroma chemicals.

Cyclohexane derivatives

Dihydromyrcenol (3,7-dimethylocta-1-en-7-ol) and carboxylic acid esters thereof are prepared from dimethylcyclooctene reactant mixtures comprising 1,5-dimethylcyclooctene in admixture with 1,6-dimethylcyclooctene and/or 1,4-dimethylcyclooctene by (a) thermally isomerizing the dimethylcyclooctene reactant mixture to afford a mixed octadiene product comprising 2,6-dimethylocta-1,7-diene in admixture with 2,7-and/or 2,5-dimethylocta-1,7-diene, (b) reacting the mixed octadiene product with a carboxylic acid to selectively form the ester of 3,7-dimethyl-octa-1-en-7-ol and (c) optionally hydrolyzing the ester of 3,7-dimethyl-octa-1-en-7-ol under basic conditions to yield dihydromyrcenol.

Preparation of dihydromyrcenol

A process for the preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol is described wherein 1,5-dimethyl-1,5-cyclooctadiene is reacted with a carboxylic acid in the optional presence of acid catalyst to form the corresponding ester of 1,5-dimethylbicyclo[3,2,1]-octan-8-ol which is subsequently hydrolyzed or alcoholyzed to the alcohol product.

Process for preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol

Esters of 1,5-dimethylbicyclo[3,2,1]octan-8-ol of the general formula: ##STR1## wherein R represents hydrogen or an aliphatic or an aromatic hydrocarbon group optionally substituted with an amino group; are useful as aroma chemicals.

Esters of 1,5-dimethylbicyclo-[3,2,1]octan-8-ol

Novel cyclooctene derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 each represents an alkyl group and R.sup.3 is hydrogen or an acyl group are disclosed along with their use as aroma chemicals and/or aroma chemical precursors and processes for their preparation.

Unsaturated alcohols and esters

Novel esters of dithiophosphoric acid and secondary alcohols having two beta quaternary carbon atoms, and salts of such esters suitable as additives in oil compositions are disclosed.

Dithiophosphoric acids and salts thereof and oil compositions containing

Novel cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.4 each represents an alkyl group and R.sup.2 and R.sup.3 each represents a hydrogen atom or alkyl group, are useful as aroma chemicals.

Cyclopentane aldehydes

Novel tertiary alcohols of the general formula: ##STR1## in which R.sub.1 represents an alkenyl or a cycloalkyl or cycloalkenyl optionally substituted by one or more alkyl groups, R.sub.2 represents hydrogen or alkyl; or R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, from a bicyclo group optionally substituted by up to two alkyl groups; R.sub.3 and R.sub.4 each represents an alkyl group, and Y represents a divalent aliphatic group of up to 4 carbon atoms, are disclosed along with their use as aroma chemicals and a process for their preparation.

Tertiary alcohols

Novel cyclohexane derivatives of the formula: ##STR1## wherein R.sup.1 represents an alkyl group, R.sup.2 and R.sup.3 each represents a hydrogen atom or an alkyl group, and X represents an epoxy or hydroxy group; are useful as aroma chemicals.

Growing community of inventors

Amsterdam, Netherlands

Aaldert J De Jong