GB871277A - Novel unsaturated ethers and a process for the manufacture and conversion thereof - Google Patents

Novel unsaturated ethers and a process for the manufacture and conversion thereof

Info

Publication number
GB871277A
GB871277A GB42211/59A GB4221159A GB871277A GB 871277 A GB871277 A GB 871277A GB 42211/59 A GB42211/59 A GB 42211/59A GB 4221159 A GB4221159 A GB 4221159A GB 871277 A GB871277 A GB 871277A
Authority
GB
United Kingdom
Prior art keywords
give
undecadiene
triethoxy
citral
trimethyl
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
GB42211/59A
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 GB871277A publication Critical patent/GB871277A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • 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
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • 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
    • 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
    • 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 ethers of formulae: <FORM:0871277/IV (b)/1> and <FORM:0871277/IV (b)/2> wherein each R represents an alkyl group containing up to six carbon atoms, the dotted lines indicating that the R groups are optional and, in particular, 6:10-dimethyl-2:2:4-triethoxy-undecadiene-(5:9), 6:9:10-trimethyl2:2:4-triethoxy-undecadiene-(5:9), 3:6:10-trimethyl-2:2:4-triethoxy-undecadiene-(5,9) and 6:10-dimethyl-2-ethoxyundecatetraene-(2:4: 6:9). The ethers may be cyclised to alpha- or beta-ionone or homologues thereof. They are prepared by acetalising citral or a homologue thereof, condensing the acetal with a 2-alkoxypropen-(1) or a 1- or 3-mono- or 1:3-di-alkyl derivative and, if desired, heating the resultant tri-ether in the presence of an acidic material to remove two molecules of alcohol to give the mono-ether. In Examples: (1) citral is reacted with ethyl orthoformate in alcohol solution in the presence of orthophosphoric acid to give citral acetal, which is reacted with 2-ethoxypropene-(1) in a solution of zinc chloride in ethyl acetate to give 6:10-dimethyl-2:2:4-triethoxy-undecadiene-(5,9), the tri-ether is dissolved in benzene together with p-toluenesulphonic acid, quinoline and hydroquinone and the mixture heated to give 6:10-dimethyl2-ethoxy-undecatetraene-(2:4:6:9) which is finally cyclised with phosphoric acid to alphaionone; (2) by the process of (1) e -methylcitral gives (6:9:10-trimethyl-2:2:4-triethoxyundecadiene-(5,9) and alpha-irone; (3) citral acetal is condensed with 2-ethoxy-butene-(2) by the process of (1) to give 3:6:10-trimethyl2:2:4-triethoxy-undecadiene-(5,9) which is treated further as in (1) to give 3:6:10-trimethyl-2-ethoxy-undecatetraene-(2:4:6:9) and isomethyl-alpha-ionone; (4) as in (3) but carrying out the de-alcoholation step in the presence of orthophosphoric acid and hydroquinone.
GB42211/59A 1958-12-17 1959-12-11 Novel unsaturated ethers and a process for the manufacture and conversion thereof Expired GB871277A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH871277X 1958-12-17

Publications (1)

Publication Number Publication Date
GB871277A true GB871277A (en) 1961-06-28

Family

ID=4544057

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42211/59A Expired GB871277A (en) 1958-12-17 1959-12-11 Novel unsaturated ethers and a process for the manufacture and conversion thereof

Country Status (1)

Country Link
GB (1) GB871277A (en)

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