GB778495A - Processes for the production of vinyl ether derivatives - Google Patents

Processes for the production of vinyl ether derivatives

Info

Publication number
GB778495A
GB778495A GB5239/56A GB523956A GB778495A GB 778495 A GB778495 A GB 778495A GB 5239/56 A GB5239/56 A GB 5239/56A GB 523956 A GB523956 A GB 523956A GB 778495 A GB778495 A GB 778495A
Authority
GB
United Kingdom
Prior art keywords
ethyl
chloride
ether
furan
vinyl ether
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
GB5239/56A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB778495A publication Critical patent/GB778495A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)

Abstract

Vinyl ether derivatives are obtained by the action of phosgene on a vinyl ether of the general formula <FORM:0778495/IV(b)/1> where R1 is an allyl radical of up to 4 carbon atoms, or with R3 forms a 4 : 5-dihydrofuran or 5 : 6-dihydropyran ring, R2 is H or an alkyl radical of up to 4 carbon atoms, and R3 is H or alkyl of up to 4 carbon atoms, or together with R1 completes a 4 : 5-dihydrofuran or 5 : 6-dihydropyran ring, at the most at room temperature, and in presence of a tertiary base not exceeding 0.2 mol. per mol. phosgene in quantity. The products in the case of the simple vinyl ether are a chlorinated ether and a b -alkoxy-acrylic chloride, and in the case of the furan and pyran compounds are a furan or pyran carboxylic chloride and a chloro-tetrahydropyran or furan, which on further treatment with alcohols or phenols give in the case of the chloro-ether an acetal, or the corresponding alkoxy or aryloxy pyran or furan, and in the case of the carboxylic chloride, an alkyl or aryl ester. In examples: (1) carbonyl chloride reacts with ethyl vinyl ether to give b -ethoxyacryloyl chloride and a -chloroethyl ether, the former of which may be converted into b -ethoxy acrylic acid or ethyl b -ethoxy acrylate; (2) carbonyl chloride reacts with ethyl ethyl-vinyl ether to give ethyl a -chlorobutyl ether, and a -ethyl-b -ethoxyacryloyl chloride, converted to a -ethyl-b -ethoxy acrylic acid by caustic soda hydrolysis, and butanal by acid hydrolysis; the ethyl ester of the a -ethyl-b -ethoxy-acrylic acid is referred to; (3) carbonyl chloride reacts with 2 : 3-dihydrofuran or 5 : 6-dihydropyran to give 2-chlorotetrahydrofuran, or 2-chlorotetrahydropyran, and 2 : 3-dihydropyran-4-carboxylic acid chloride or 5 : 6-vinyl ethers specified include butyl and allyl vinyl ethers, and the product from 2-methyl-4 : 5-dihydrofuran and carbonyl chloride is converted directly into 2-methyl-2-ethoxytetrahydrofuran and ethyl 2-methyl-4 : 5-dihydro - furan - 3 - carboxylate. Specification 570,974, [Group IV], is referred to.
GB5239/56A 1955-03-04 1956-02-20 Processes for the production of vinyl ether derivatives Expired GB778495A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR778495X 1955-03-04

Publications (1)

Publication Number Publication Date
GB778495A true GB778495A (en) 1957-07-10

Family

ID=9202210

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5239/56A Expired GB778495A (en) 1955-03-04 1956-02-20 Processes for the production of vinyl ether derivatives

Country Status (1)

Country Link
GB (1) GB778495A (en)

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