GB886364A - 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
GB886364A
GB886364A GB5399/60A GB539960A GB886364A GB 886364 A GB886364 A GB 886364A GB 5399/60 A GB5399/60 A GB 5399/60A GB 539960 A GB539960 A GB 539960A GB 886364 A GB886364 A GB 886364A
Authority
GB
United Kingdom
Prior art keywords
group
hydroxy
methyl
aluminium hydride
lithium aluminium
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
GB5399/60A
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 GB886364A publication Critical patent/GB886364A/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
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Alcohols and esters of the general formula CH3-R1-CH=CH-CH=CH-R2-X1 in which X1 is a hydroxy-methyl or esterified hydroxy-methyl group and R1 and R2 are alkylene groups together containing 8-12 carbon atoms, are obtained by reacting a Grignard or alkali-metal derivative of acetylene with one of the aldehydes of the general formulae CH3-R1-CHO and X2-R2-CHO in which X2 is a carboxyl, alkoxycarbonyl, hydroxymethyl, acetal or etherified or esterified hydroxymethyl group, reacting a Grignard or alkali metal derivative of the reaction product with the other aldehyde reducing the acetylenic glycol of the formula <FORM:0886364/IV (b)/1> thus obtained and, where necessary, converting the group X2 into a hydroxy-methyl or acyloxymethyl group in a manner known per se. Preferably, the reactions with alkali metal derivatives are carried out in liquid ammonia. The acetylenic glycol may be reduced by a metal hydride, e.g. lithium aluminium hydride, in the presence of an organic base, e.g. N,N-diethylaniline. When X2 is an esterified or etherified hydroxy-methyl group it can be converted into a hydroxy-methyl group by hydrolysis, when it is an acetal group it can be converted to a hydroxy-methyl group by acid hydrolysis followed by reduction of the resulting aldehyde with lithium aluminium hydride, and if X2 is an alkoxy carbonyl group it may be reduced to a hydroxymethyl group by reduction with lithium aluminium hydride. In an example, a lithium derivative of acetylene is reacted with butyraldehyde to give hexyn-(1)-ol-(3) which is added to a Grignard solution obtained by reacting magnesium and ethyl bromide in ether; 9-oxo-nonanoic-(1) acid methyl ester is added and 10,13-dihydroxyhexadecyn-(11)-oic-(1) acid methyl ester is separated; the ester is then reduced with lithium aluminium hydride and hydrolysed with sulphuric acid to give hexadecadien-(10,12)-ol-(1).
GB5399/60A 1959-02-16 1960-02-16 A process for the manufacture of unsaturated alcohols and acyl derivatives thereof Expired GB886364A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH81460A CH390902A (en) 1959-02-16 1959-02-16 Process for the production of unsaturated alcohols

Publications (1)

Publication Number Publication Date
GB886364A true GB886364A (en) 1962-01-03

Family

ID=4195798

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5399/60A Expired GB886364A (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) BE587616A (en)
CH (1) CH390902A (en)
DE (1) DE1124478C2 (en)
FR (1) FR1247683A (en)
GB (1) GB886364A (en)
NL (2) NL246469A (en)

Also Published As

Publication number Publication date
BE587616A (en) 1900-01-01
FR1247683A (en) 1960-10-24
CH390902A (en) 1965-04-30
DE1124478C2 (en) 1962-09-27
DE1124478B (en) 1962-03-01
NL246469A (en) 1900-01-01
NL108700C (en) 1900-01-01

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