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US 6,150,538 AGranted
Process for manufacturing cis-isoambrettolide and use thereof
AssigneeSynarome
InventorClaude Delphis
Life of this patent
Estimating the term…
Abstract
Manufacture of a molecule which is of important olfactory interest for perfumers. This molecule belongs to the group of macrocyclic lactones with a musk odor. The manufacturing process consists in preparing cis-16-hydroxy-9-hexadecenoic acid or an ester of this acid, which is a precursor of cis-isoambrettolide, the latter being obtained by macrolactonization in a very high degree of purity. Use as a fragrance material.
Claims16
A process for manufacturing cis-isoambrettolide comprising:
- (a) providing trans-16-hydroxy-9-hexadecenoic acid or acid ester having the formula:
- ##STR4## wherein R.sup.1 is selected from the group consisting of hydrogen and an acetyl radical and R.sup.2 is selected from the group consisting of hydrogen and a methyl radical;
- (b) contacting said acid or acid ester with a mixture of a peroxide and a carboxylic acid to form the epoxide of the said acid or acid ester;
- (c) subjecting said epoxide to hydrolysis in the presence of an acidic or basic medium to form erythro-aleuritic acid or acid ester;
- (d) heating said acid or acid ester in the presence of an ortho ester having the formula HC(OR.sup.3).sub.3, where R.sup.3 is selected from the group consisting of a methyl and ethyl radical, to form the dioxolane;
- (e) subjecting said dioxolane to pyrolysis treatment in the presence or absence of organic solvent to form cis-16-hydroxyhexadecenoic acid or acid ester having the formula:
- ##STR5## and, (f) subjecting the acid or acid ester product from step (e) to macrolactonization conditions.
4 more elements
A process for manufacturing cis-isoambrettolide comprising:
- (a) providing trans-16-hydroxy-9-hexadecenoic acid or acid ester having the formula:
- ##STR6## wherein R.sup.1 is selected from the group consisting of hydrogen and an acetyl radical and R.sup.2 is selected from the group consisting of hydrogen and a methyl radical;
- (b) contacting said acid or acid ester with a mixture of a peroxide and a carboxylic acid to form the epoxide of said acid or acid ester;
- (c) subjecting said epoxide to alcoholysis in the presence of an R'OH alcohol, wherein R' is selected from the group consisting of a methyl and ethyl radicals, to form a mixture of beta-hydroxy ethers;
- (d) heating said ether mixture in the presence of an ortho ester having the formula HC(OR.sup.3).sub.3, where R.sup.3 is selected from the group consisting of a methyl and ethyl radical, to form the dioxolane;
- (e) subjecting said dioxolane to pyrolysis treatment in the presence or absence of organic solvent to form cis-16-hydroxyhexadecenoic acid or acid ester having the formula:
- ##STR7## and, (f) subjecting the acid or acid ester product from step (e) to macrolactonization conditions.
4 more elements
Dependencies are inferred from the claim text.