GB859898A - Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols - Google Patents

Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols

Info

Publication number
GB859898A
GB859898A GB1712559A GB1712559A GB859898A GB 859898 A GB859898 A GB 859898A GB 1712559 A GB1712559 A GB 1712559A GB 1712559 A GB1712559 A GB 1712559A GB 859898 A GB859898 A GB 859898A
Authority
GB
United Kingdom
Prior art keywords
unsaturated alcohols
undecadiyn
integer
alcohols
ethylenically unsaturated
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
GB1712559A
Inventor
Peter George Philpott
John Mervyn Osbond
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB1712559A priority Critical patent/GB859898A/en
Publication of GB859898A publication Critical patent/GB859898A/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
    • C07C29/32—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 without formation of -OH groups
    • 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
    • C07C29/36—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
    • 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
    • C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds

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

Abstract

The invention comprises alcohols of the general formula: <FORM:0859898/IV(b)/1> where m is an integer from 2 to 5 and n an integer from 0 to 8, specifically undecadiyn(2, 5)-ol-1, tetradecatriyn -(2, 5, 8)-ol-1, eicosatetrayne- (5, 8, 11, 14)-ol-(1), and nonadecatetrayne- (4, 7, 10, 13)-ol-(1), which are prepared either (1) by condensing a halogen compound CH3-(CH2)4-(C­C-CH2)m - 1X, where X is chlorine, bromine or iodine in the presence of a cuprous salt with an alcohol CH sDC-(CH2)n + 1OH, in a Grignard reaction, or (2) where n has a value of 2 to 8, by reducing an acid <FORM:0859898/IV(b)/2> where p is an integer from 1 to 7, with lithium aluminium hydride and reducing the metal complex formed. The alcohols may be partially reduced by catalytic hydrogenation, e.g. by lead inhibited palladium catalysts to ethylenically unsaturated alcohols. Examples describe the preparation of undecadiyn-(2, 5)-ol-(1) and tetradecatriyn -(2, 5, 8)-ol-(1) from propargyl alcohol and 1-bromo-octyne-(2) and undecadiyn-(2, 5)-yl bromide respectively; of eicosatetrayne-(5, 8, 11, 14)-ol-(1) and nonadecatetrayne -(4, 7, 10, 13)-ol-(1) by condensing hexyn-(5)-ol-(1) and pentyne -(4)-ol-(1) with 1-bromo-tetradecatriyne -(2, 5, 8) in a Grignard reaction; and of eicosatretrayn -(5, 8, 11, 14)-ol-(1) by the reduction of a complex of eicosatetrayn -(5, 8, 11, 14)-oic acid with lithium aluminium hydride.
GB1712559A 1958-07-05 1958-07-05 Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols Expired GB859898A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1712559A GB859898A (en) 1958-07-05 1958-07-05 Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1712559A GB859898A (en) 1958-07-05 1958-07-05 Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols

Publications (1)

Publication Number Publication Date
GB859898A true GB859898A (en) 1961-01-25

Family

ID=10089719

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1712559A Expired GB859898A (en) 1958-07-05 1958-07-05 Novel acetylenically unsaturated alcohols and a process for the manufacture thereof and for the conversion thereof into the corresponding ethylenically unsaturated alcohols

Country Status (1)

Country Link
GB (1) GB859898A (en)

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