[go: up one dir, main page]

GB911106A - A process for the manufacture of unsaturated alcohols and acyl derivatives thereof - Google Patents

A process for the manufacture of unsaturated alcohols and acyl derivatives thereof

Info

Publication number
GB911106A
GB911106A GB540160A GB540160A GB911106A GB 911106 A GB911106 A GB 911106A GB 540160 A GB540160 A GB 540160A GB 540160 A GB540160 A GB 540160A GB 911106 A GB911106 A GB 911106A
Authority
GB
United Kingdom
Prior art keywords
cis
trans
group
methyl
hydroxy
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
GB540160A
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 GB911106A publication Critical patent/GB911106A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/18—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
    • 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
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • 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
    • C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
    • 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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

Landscapes

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

Abstract

Alcohols and esters of the general formula CH3-R1-A-R2-X1, where A represents -CH2-CH=CH-CH=CH- or -CH=CH-CH=CH-CH2-, and R1 and R2 represent straight chain alkylene groups which collectively contain from 7 to 11 carbon atoms and X1 represents a hydroxy-methyl or aliphatic acyloxy group, are prepared by partially hydrogenating a diacetylenic compound, CH3-R1-C­C-CH2-C­R2-X2, wherein X2 represents, a hydroxy-methyl, an etherified or esterified hydroxy-methyl group, a carboxy or esterified carboxy group, or an aldehyde or acetalised aldehyde group, in the presence of a catalyst to form a compound, CH3-R1-CH=CH-CH2-CH=CH-R2-X2 and in either sequence where the two steps are involved, isomerising the partially hydrogenated product by treatment with a strongly alkaline agent, and transforming, if necessary, the group X2 therein into a hydroxy-methyl or aliphatic acyloxy-methyl group by conventional methods. The partial hydrogenation may be in the presence of lead-inhibited palladium catalyst, and the isomerization carried out using strong alkalis at elevated temperatures, preferably in an anhydrous solvent such as butanol, ethylene glycol or glycerine, or by treating with sodium or potassium amide in liquid ammonia between, for example -30 DEG C. and +20 DEG C. In Examples (1) a mixture of tetradecadien-(6 trans, 8 cis)-ol-(1) and -(5 cis, 7 trans)-ol-(1) is obtained by the hydrogenation and isomerisation of tetradecadiyn-(5,8)-ol-(1), (2) tetradecadien-(5,8)-ol-(1) is obtained from tetradecadiyn-(5,8)-oic-(1) acid, (3) a mixture of hexadecadien-(10 cis, 12 trans)-ol-(1), and -(11 trans, 13 cis)-ol-(1) from hexadecadiyn-(10,13)-oic-(1) acid and (4) a mixture of hexadecadien-(9 cis, 11 trans)-ol-(1) and -(10 trans, 12 cis)-ol-(1) from hexadecadiyn-(9,12)-oic-(1) acid. The compounds have insect attracting properties and in particular hexadecadien-(10,12)-ol-(1), are suitable for mixing with insecticides. Specification 911,107 is referred to.
GB540160A 1959-02-16 1960-02-16 A process for the manufacture of unsaturated alcohols and acyl derivatives thereof Expired GB911106A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH6962059A CH390901A (en) 1959-02-16 1959-02-16 Process for the preparation of unsaturated alcohols or esters

Publications (1)

Publication Number Publication Date
GB911106A true GB911106A (en) 1962-11-21

Family

ID=4529653

Family Applications (1)

Application Number Title Priority Date Filing Date
GB540160A Expired GB911106A (en) 1959-02-16 1960-02-16 A process for the manufacture of unsaturated alcohols and acyl derivatives thereof

Country Status (6)

Country Link
BE (1) BE587618A (en)
CH (1) CH390901A (en)
DE (1) DE1111615B (en)
FR (1) FR1248761A (en)
GB (1) GB911106A (en)
NL (1) NL248470A (en)

Also Published As

Publication number Publication date
NL248470A (en)
BE587618A (en)
FR1248761A (en) 1960-12-23
DE1111615B (en) 1961-07-27
CH390901A (en) 1965-04-30

Similar Documents

Publication Publication Date Title
GB911106A (en) A process for the manufacture of unsaturated alcohols and acyl derivatives thereof
GB857081A (en) Cyclopentanophenanthrene derivatives and process for the production thereof
US3278588A (en) Lower alkanoyl esters of 4-hydroxy-2-lower alkyl cyclopentane-1, 3-diones
DE868154C (en) Process for the preparation of sulfosuccinic acid esters
US3379762A (en) Desacetylamino colchicine derivatives
Toda et al. Cyclic Acetylenes. I. Cyclic Derivatives of o, o′-Dihydroxydiphenyl-diacetylene. An Example of a Strained Cyclic Diacetylene
US2811549A (en) Process of preparing high solids beta-alanine detergents
DE892443C (en) Process for the preparation of ª‡-haloacrylic acid esters
GB671563A (en) Improvements in or relating to the fractionation of stereoisomers
DE870409C (en) Process for the production of 3-ketones of the androstane and pregnane series
DE848941C (en) Methods of washing, wetting or dispersing
US2071804A (en) Acyl octahydrofollicle hormones and their production
US3206458A (en) 19-substituted pregnenes
DE855861C (en) Process for the production of dioxytetrahydrofurans
GB695504A (en) Method of isolating and purifying cholic and desoxycholic acids
GB912036A (en) 11-methylene-5ª--steroids
GB455018A (en) Process for the manufacture of esters of polycyclic alcohols
GB455019A (en) Process for the manufacture of esters of polycyclic alcohols
GB971049A (en) Novel cyclopentanophenanthrene compounds and a process for the production thereof
GB913903A (en) Alkanoic acid esters and process for their preparation
GB566653A (en) Processes for the synthesis of pyrazine-monocarboxylamide
GB1117456A (en) 1ªß-methyl-2,3ª‡-methylene steroids and a process for their manufacture
GB791543A (en) Process for the production of 2-methylol-3-ketobutene(1,2)
GB566006A (en) Improvements in or relating to the production of alpha-chloro, beta-hydroxynitriles
GB452447A (en) The production of acyl derivatives of germinal gland hormone preparations