GB1121508A - Unsaturated alcohols and the esters thereof - Google Patents

Unsaturated alcohols and the esters thereof

Info

Publication number
GB1121508A
GB1121508A GB51891/65A GB5189165A GB1121508A GB 1121508 A GB1121508 A GB 1121508A GB 51891/65 A GB51891/65 A GB 51891/65A GB 5189165 A GB5189165 A GB 5189165A GB 1121508 A GB1121508 A GB 1121508A
Authority
GB
United Kingdom
Prior art keywords
vinyl
hydrogen
compounds
perfume
octen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB51891/65A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Publication of GB1121508A publication Critical patent/GB1121508A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/04—Formic acid esters
    • C07C69/06—Formic acid esters of monohydroxylic compounds
    • C07C69/07—Formic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1121508/C2/1> wherein X represents hydrogen or <FORM:1121508/C2/2> in which R is hydrogen or a C1- 4 alkyl, and Y is a vinyl or ethyl group. The compounds are made by thermal isomerization of hydronopol to yield 7 - methyl - 3 - vinyl - octen - (6)-ol-(1), followed, if desired, by esterification with a C1- 5 carboxylic acid or by reduction of the vinyl group to give 7-methyl-3-ethyl-octen-(6)-ol-(1) which may be subsequently esterified. The partial reduction of the 3-vinyl compound may be effected using hydrogen and, e.g. Raney Ni, or by reaction with an organo-aluminium compound, e.g. di-isobutyl-aluminium hydride, followed by hydrolysis. Esterification is effected by known methods, e.g. with the free carboxylic acid and p-toluene sulphonic acid, or with the acid halide in the presence of a base. The formates and acetates of the alcohols are prepared. The compounds have floral odours and are used in perfume compositions (see Division A5).ALSO:The invention comprises perfume constituents having the general formula <FORM:1121508/A5-A6/1> wherein X represents hydrogen or <FORM:1121508/A5-A6/2> , in which R is hydrogen or a C1-4 alkyl, and Y represents a vinyl or ethyl group. These compounds have a floral odour. Examples of perfume formulations containing the novel constituents and other known components are provided.
GB51891/65A 1964-12-16 1965-12-07 Unsaturated alcohols and the esters thereof Expired GB1121508A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH36267A DE1234900B (en) 1964-12-16 1964-12-16 Fragrance composition

Publications (1)

Publication Number Publication Date
GB1121508A true GB1121508A (en) 1968-07-31

Family

ID=7433799

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51891/65A Expired GB1121508A (en) 1964-12-16 1965-12-07 Unsaturated alcohols and the esters thereof

Country Status (4)

Country Link
CH (1) CH473889A (en)
DE (1) DE1234900B (en)
FR (1) FR1459656A (en)
GB (1) GB1121508A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5024847A (en) * 1989-09-18 1991-06-18 Basf K&F Corporation Sulfur containing acyclic terpenes
EP2969020B1 (en) * 2013-03-15 2017-11-29 The Procter and Gamble Company Specific unsaturated and branched functional materials for use in consumer products

Also Published As

Publication number Publication date
DE1234900B (en) 1967-02-23
FR1459656A (en) 1966-11-18
CH473889A (en) 1969-06-15

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