GB633972A - Preparation of alkynyl-alkenylcarbinols - Google Patents

Preparation of alkynyl-alkenylcarbinols

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Publication number
GB633972A
GB633972A GB26115/47A GB2611547A GB633972A GB 633972 A GB633972 A GB 633972A GB 26115/47 A GB26115/47 A GB 26115/47A GB 2611547 A GB2611547 A GB 2611547A GB 633972 A GB633972 A GB 633972A
Authority
GB
United Kingdom
Prior art keywords
alkynyl
give
brom
alkali metal
ammonia
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
GB26115/47A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB26115/47A priority Critical patent/GB633972A/en
Publication of GB633972A publication Critical patent/GB633972A/en
Expired legal-status Critical Current

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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

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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

Alkynyl-alkenylcarbinols are prepared by reacting a haloepoxyalkane of the formula <FORM:0633972/IV (b)/1> where X is Cl or Br, and R, R1 are H, CH3 or C2H5, in liquid ammonia with an alkali metal derivative of an alkynyl hydrocarbon of the formula Y-C­CM, where Y is H or an alkyl or aryl group, and M is an alkali metal. Preferably, reaction is effected at the boiling point of the ammonia using a molar excess of the alkali metal derivative. An atmosphere of inert gas such as nitrogen may be used. Reaction times are suitably 5-18 hours. Suitable alkynyl hydrocarbons are acetylene, phenylacetylene, and 1-hexyne, and suitable haloepoxyalkanes are epichlor- (or brom-) hydrin, and brom-2,3-epoxybutane. In examples: (1) sodium is dissolved in liquid ammonia in presence of ferric nitrate to form sodamide, the solution being saturated with acetylene to give sodium acetylide, epichlorhydrin then being added while cooling, ammonium chloride added, ammonia evaporated, and pent-2-en-4-yn-1-ol extracted with ether; (2) epibromhydrin is reacted similarly, yielding the same alkynyl carbinol and a compound of unknown structure; (3) 1-brom-2,3-epoxybutane yielded hex-3-en-5-yn-2-ol, and 2-(2,3-epoxy-1-butoxy)-hex-3-en-5-yne; (4) phenylacetylene is used in a similar process to (1), yielding 5-phenylpent-2-en-4-yn-1-ol; (5) 1-hexyne similarly gives non-2-en-4-yn-1-ol. The products may be partially or completely hydrogenated to give, for example, a dienol; treated with mercury sulphate and sulphuric acid to give a furane derivative; with an amine and formaldehyde to effect the Mannich reaction; oxidized to the corresponding carboxylic acid, for example with chromic acid in acetone; subjected to oxidative coupling in presence of cuprous ammonium chloride to give the p di-yne-glycol which may be hydrogenated to the corresponding alkane diol; or condensed with formaldehyde in presence of cuprous hydroxide.
GB26115/47A 1947-09-26 1947-09-26 Preparation of alkynyl-alkenylcarbinols Expired GB633972A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB26115/47A GB633972A (en) 1947-09-26 1947-09-26 Preparation of alkynyl-alkenylcarbinols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB26115/47A GB633972A (en) 1947-09-26 1947-09-26 Preparation of alkynyl-alkenylcarbinols

Publications (1)

Publication Number Publication Date
GB633972A true GB633972A (en) 1949-12-30

Family

ID=10238606

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26115/47A Expired GB633972A (en) 1947-09-26 1947-09-26 Preparation of alkynyl-alkenylcarbinols

Country Status (1)

Country Link
GB (1) GB633972A (en)

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