GB866691A - Novel pentenyne derivatives and a process for the manufacture thereof - Google Patents

Novel pentenyne derivatives and a process for the manufacture thereof

Info

Publication number
GB866691A
GB866691A GB4210/59A GB421059A GB866691A GB 866691 A GB866691 A GB 866691A GB 4210/59 A GB4210/59 A GB 4210/59A GB 421059 A GB421059 A GB 421059A GB 866691 A GB866691 A GB 866691A
Authority
GB
United Kingdom
Prior art keywords
acid
toluene sulphonic
acetalising
alkoxy
preparation
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
GB4210/59A
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 GB866691A publication Critical patent/GB866691A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group

Landscapes

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

Abstract

The invention comprises compounds of the formula: <FORM:0866691/IV (b)/1> and their preparation by reacting a 1,1,3,3-tetraalkoxy-2-methylpropane with an equimolar amount of water in the presence of an acid, condensing the resulting 1-alkoxy-2-methylpropen-(1)-ol-(3) by means of an organometallic reaction with acetylene, and transforming the 1-alkoxy-2-methyl-3-hydroxypenten-(1)-yne-(4) so formed into the required substances by treatment with an acetalising agent in the presence of an acidic agent. The reaction with water is preferably carried out in the presence of a strong acid such as sulphuric or p-toluene sulphonic. The condensation step may be carried out in liquid ammonia using an alkali metal or alkaline earth metal acetylide. Suitable acetalising agents are esters of ortho acids (e.g. orthoformic acid ethyl ester) or glycols (e.g. ethylene glycol); suitable acids are p-toluene sulphonic acid and, for acylic acetals, phosphonic acid containing a trace of p-toluene sulphonic acid; it is advantageous to carry out the preparation in the presence of an alkanol. Specification 845,820 is referred to.
GB4210/59A 1958-02-13 1959-02-06 Novel pentenyne derivatives and a process for the manufacture thereof Expired GB866691A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH866691X 1958-02-13

Publications (1)

Publication Number Publication Date
GB866691A true GB866691A (en) 1961-04-26

Family

ID=4543704

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4210/59A Expired GB866691A (en) 1958-02-13 1959-02-06 Novel pentenyne derivatives and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB866691A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5471005A (en) * 1994-11-18 1995-11-28 Loyola University Of Chicago Method of making 2,7-dimethyl-2,4,6-octatrienedial, a key intermediate in the commercial syntheses of various carotenoids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5471005A (en) * 1994-11-18 1995-11-28 Loyola University Of Chicago Method of making 2,7-dimethyl-2,4,6-octatrienedial, a key intermediate in the commercial syntheses of various carotenoids

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