GB866693A - Novel ether-acetals and a process for the manufacture thereof - Google Patents

Novel ether-acetals and a process for the manufacture thereof

Info

Publication number
GB866693A
GB866693A GB17543/60A GB1754360A GB866693A GB 866693 A GB866693 A GB 866693A GB 17543/60 A GB17543/60 A GB 17543/60A GB 1754360 A GB1754360 A GB 1754360A GB 866693 A GB866693 A GB 866693A
Authority
GB
United Kingdom
Prior art keywords
methyl
penten
acetals
condensing
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
GB17543/60A
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 GB866693A publication Critical patent/GB866693A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • 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
    • C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms

Landscapes

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

Abstract

The invention comprises acetals of 3-alkoxy4-methyl-hepten-(4)-yn-(6)-al-(1), such as the diethoxy-, di-isopropoxy or ethylenedioxy acetals, and their preparation by condensing an acetal of 2-methyl-penten-(2)-yn-(4)-al-(1) with a vinyl alkyl ether, preferably in an inert solvent such as benzene, ether or petroleum ether in the presence of an acidic catalyst such as zinc chloride or boron trifluoride etherate. 2-Methyl-penten-(2)-yn-(4)-al-(1), diethyl acetal is made by condensing ethyl orthoformate with a propenyl ether in the presence of boron trifluoride etherate, hydrolysing the resulting 1:1:3:3-tetraethoxy-2-methyl-propene, esterifying the methyl malonic dialdehyde obtained to give 1-ethoxy-2-methyl-propen-(1)-al-(3), condensing with an alkali or alkaline earth metal acetylide to give 1-ethoxy-2-methyl-3-hydroxy-penten-(1)-yne-(4) and treating with ethyl orthoformate in the presence of p-toluenesulphonic and phosphoric acids. Other acetals of this type are similarly prepared. Cyclic 2-methyl-penten-(2)-yn-(4)-al-(1), ethylene glycol acetal is prepared by condensing 1-ethoxy-2-methyl-3-hydroxy-penten-(1)-yne -(4) with ethylene glycol.
GB17543/60A 1958-02-14 1959-02-13 Novel ether-acetals and a process for the manufacture thereof Expired GB866693A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH866693X 1958-02-14

Publications (1)

Publication Number Publication Date
GB866693A true GB866693A (en) 1961-04-26

Family

ID=4543706

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17543/60A Expired GB866693A (en) 1958-02-14 1959-02-13 Novel ether-acetals and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB866693A (en)

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