# US 4,399,062 A · Branched chain olefinic alcohols, thiols, esters and ethers, organoleptic uses thereof, processes for preparing same and intermediates therefor

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,399,062 A
- Document ID: US4399062A
- Status: Granted
- Kind: A
- Application number: 06/322,841
- Filed: 1981-11-19
- Granted: 1983-08-16
- Earliest claimed: 1980-12-04
- Assignees: International Flavors & Fragrances Inc.
- Inventors: Richard M. Boden
- Web page: https://patentgrep.com/patent/US4399062A

## CPC

- C11D 3/3956: {Liquid compositions}
- A23L 27/2026: {Hydroxy compounds}
- A24B 15/32: by acyclic compounds
- C07C 29/40: with compounds containing carbon-to-metal bonds
- C07C 45/455: {with carboxylic acids or their derivatives}
- C11B 9/0007: {Aliphatic compounds}
- C11D 1/24: containing ester or ether groups directly attached to the nucleus
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A24B: MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)

## Abstract

Described are compounds defined according to the structure: ##STR1## taken alone or in admixture wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines are carbon-carbon single bonds; wherein R.sub.1 represents C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.1 -C.sub.4 alkyl; Z represents oxygen or sulfur; R.sub.3 represents hydrogen, MgX, Li, C.sub.1 -C.sub.3 lower alkyl or C.sub.1 -C.sub.3 lower acyl; and wherein X represents chloro, bromo or iodo and uses thereof in augmenting or enhancing the aroma and/or taste of consumable materials such as perfume compositions, colognes, perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or dryer-added fabric softener articles, smoking tobaccos, chewing gums, chewing tobaccos, medicinal products or toothpastes. Also described are processes for preparing such compounds hereinafter described as branched chain olefinic alcohols, thiols, esters and ethers.

## Claims

### Claim 1

A process for augmenting or enhancing the aroma of a perfume composition or cologne comprising the step of adding to a perfume base or a cologne base an aroma augmenting or enhancing quantity of at least one branched chain olefinic chalcogen derivative having the formula: ##STR124## wherein Z represents oxygen or sulfur; 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; wherein R.sub.1 represents C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.1 -C.sub.4 alkyl; R.sub.3 represents hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.1 -C.sub.3 lower acyl.

### Claim 2 (depends on 1)

The process of claim 1 wherein the compound added to the perfume base or cologne base has the structure: ##STR125##

### Claim 3 (depends on 1)

The process of claim 1 wherein the compound added to the perfume base or cologne base has the structure: ##STR126##

### Claim 4 (depends on 1)

The process of claim 1 wherein the compound added to the perfume base or cologne base has the structure: ##STR127##

### Claim 5 (depends on 1)

The process of claim 1 wherein the compound added to the perfume base or cologne base has the structure: ##STR128##

### Claim 6 (depends on 1)

The process of claim 1 wherein the material added to the perfume composition or cologne is a composition of matter comprising a major proportion of compounds defined according to the structure: ##STR129## 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: ##STR130## 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: ##STR131## 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: ##STR132## 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.