GB960756A - Novel unsaturated alcohols and a process for the manufacture thereof - Google Patents

Novel unsaturated alcohols and a process for the manufacture thereof

Info

Publication number
GB960756A
GB960756A GB48080/62A GB4808062A GB960756A GB 960756 A GB960756 A GB 960756A GB 48080/62 A GB48080/62 A GB 48080/62A GB 4808062 A GB4808062 A GB 4808062A GB 960756 A GB960756 A GB 960756A
Authority
GB
United Kingdom
Prior art keywords
group
alkyl group
carbon atoms
methyl group
optional
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
GB48080/62A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB960756A publication Critical patent/GB960756A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • 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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • 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
    • 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
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0960756/C1/1> in which the broken lines denote optional bonds, R1 is a phenyl group or an alkyl group containing 2-4 carbon atoms in the case of trienes in which the optional methyl group is absent and/or otherwise an alkyl group containing 1-4 carbon atoms, and R2 is a methyl group or together with R1 a pentamethylene group. They are prepared by halogenating an alcohol of formula: <FORM:0960756/C1/2> by known methods to replace the OH group by a halogen atom with allyl rearrangement, converting the product by treatment with an inorganic salt of an alkane carboxylic acid containing 1-5 carbon atoms into a carboxylic ester and hydrolyzing the ester with an aqueous alcoholic solution of an inorganic base. Preferred tertiary alcohol starting materials are 3, 7, 11-trimethyl-tridecatrien-(1, 6, 10)-ol-13), 3, 7, 10, 11-tetramethyl-dodcecatrien-(1, 6, 10)-ol-(3) and 3, 7, 11-trimethyl-dodcecadien-(1,6)-ol-(3). The halogenation may be carried out by treating the tertiary alcohol with concentrated aqueous hydrochloric or hydrobromic acid, phosphorus tribromide or anhydrous hydrogen chloride or bromide. The halogenation is accompanied by an allyl rearrangement resulting in the formation of 1-halo compounds.ALSO:Alcohols of general formula <FORM:0960756/A5-A6/1> in which the broken lines denote optional bonds, R1 is a phenyl group or a C2-C4 alkyl group in the case of trienes in which the optional methyl group is absent but otherwise a C1-C4 alkyl group and R2 is a methyl group or, together with R1 a pentamethylene group, may be used as insecticidal ingredients in mixtures for combating insects. They may be used in admixture with other insecticides and in emulsions, suspension, dusts, solutions or aerosol sprays.
GB48080/62A 1961-12-22 1962-12-20 Novel unsaturated alcohols and a process for the manufacture thereof Expired GB960756A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1486861A CH412858A (en) 1961-12-22 1961-12-22 Process for the production of polyolefinic alcohols

Publications (1)

Publication Number Publication Date
GB960756A true GB960756A (en) 1964-06-17

Family

ID=4404431

Family Applications (1)

Application Number Title Priority Date Filing Date
GB48080/62A Expired GB960756A (en) 1961-12-22 1962-12-20 Novel unsaturated alcohols and a process for the manufacture thereof

Country Status (6)

Country Link
BE (1) BE625929A (en)
CH (1) CH412858A (en)
DE (1) DE1191365B (en)
FR (1) FR1344638A (en)
GB (1) GB960756A (en)
NL (1) NL286966A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4292454A (en) 1977-12-29 1981-09-29 Scm Corporation Coupling reaction involving a Grignard and allylic halide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH360384A (en) * 1956-07-30 1962-02-28 Hoffmann La Roche Process for the production of polyolefinic alcohols

Also Published As

Publication number Publication date
CH412858A (en) 1966-05-15
FR1344638A (en) 1963-11-29
BE625929A (en) 1963-06-11
DE1191365B (en) 1965-04-22
NL286966A (en)

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