# US 4,395,370 A · Branched chain alkenyl methyl carbonates, uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles and formate intermediates useful in preparing same

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- Number: US 4,395,370 A
- Document ID: US4395370A
- Status: Granted
- Kind: A
- Application number: 06/329,222
- Filed: 1981-12-10
- Granted: 1983-07-26
- Earliest claimed: 1981-12-10
- Assignees: International Flavors & Fragrances Inc.
- Inventors: Richard M. Boden; Theodore J. Tyszkiewicz; Michael Licciardello
- Web page: https://patentgrep.com/patent/US4395370A

## CPC

- C11B 9/0015: {containing oxygen as the only heteroatom}
- C07C 45/46: Friedel-Crafts reactions
- C07C 67/02: by interreacting ester groups, i.e. transesterification
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 69/96: Esters of carbonic or haloformic acids
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Described are branched chain alkenyl methyl carbonates and branched chain alkenyl formates defined according to the structure: ##STR1## wherein R.sub.3 represents hydrogen or methoxy and wherein in each of the molecules described by the structure, one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond; and uses of the compounds wherein R.sub.3 is methoxy in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair sprays, shampoos, bath oils and plastic fragrances.

## Claims

### Claim 1

An ester defined according to the structure: ##STR69## wherein 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.

### Claim 2

A mixture produced according to the process of:
(a) dimerizing isoamylene in order to form a mixture of diisoamylene isomers defined according to the structure: ##STR70## wherein R.sub.1 ", R.sub.2 ", R.sub.3 ", R.sub.4 " and R.sub.5 " represent 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) acetylating the resulting diisoamylene derivative with acetic anhydride or an acetyl halide in order to form a mixture of compounds defined according to the structure: ##STR71## (c) reducing the resulting compound in order to form a mixture of carbinols defined according to the structure: ##STR72## (d) reacting the resulting carbinol with formic acid in order to form a formate defined according to the structure: ##STR73## (e) reacting the resulting formate with dimethyl carbonate in order to form the compounds defined according to the structure: ##STR74##