GB392062A - An improved process for the conversion of alicyclic ketones into unsaturated aldehydes - Google Patents

An improved process for the conversion of alicyclic ketones into unsaturated aldehydes

Info

Publication number
GB392062A
GB392062A GB27932/32A GB2793232A GB392062A GB 392062 A GB392062 A GB 392062A GB 27932/32 A GB27932/32 A GB 27932/32A GB 2793232 A GB2793232 A GB 2793232A GB 392062 A GB392062 A GB 392062A
Authority
GB
United Kingdom
Prior art keywords
trimethylcycloheptene
aldehyde
acetal
ester
trimethylcycloheptane
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
GB27932/32A
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.)
M Naef & Cie SA
Original Assignee
M Naef & Cie 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 M Naef & Cie SA filed Critical M Naef & Cie SA
Publication of GB392062A publication Critical patent/GB392062A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

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

Abstract

Unsaturated alicyclic aldehydes are prepared from saturated alicyclic ketones by first condensing them with a formic acid ester, converting the resulting hydroxymethylene compound by condensation with orthoformic acid ethyl ester into the keto-acetal, reducing the latter to the hydroxyacetal, splitting off water to the unsaturated acetal by heat treatment of the xanthogenic ester, and finally hydrolysing the acetal group. Examples are given of the preparation of 1 : 1 : 7-trimethylcycloheptene-2-aldehyde-3 from 1 : 1 : 7-trimethylcycloheptane-2- one (obtained by heating the thorium salt of 2 : 3-dimethylheptane-2 : 7-dicarboxylic acid in vacuo), and of a mixture of 1 : 1 : 6-trimethylcycloheptene-3-aldehyde-4 and 1 : 1 : 6-trimethylcycloheptene-2-aldehyde-2 from 1 : 1 : 6-trimethylcycloheptane-3- one. In each case isoamyl formate is used as the formic acid ester, sodium and aqueous ether as the reducing agent, carbon disulphide in the presence of potassium and amylene hydrate (followed by alkylation with methyl iodide) for producing the alkyl xanthogenate, and sulphuric acid as the hydrolysing agent. The Specification as open to inspection under Sect. 91 describes also the production of the mixture of 1 : 1 : 6-trimethylcycloheptene-3-aldehyde-4 and 1 : 1 : 6-trimethylcycloheptene-2-aldehyde-2 directly from the corresponding hydroxyacetats by treatment with thionyl chloride in the presence of dimethylaniline. This subject-matter does not appear in the Specification as accepted.
GB27932/32A 1931-10-30 1932-10-07 An improved process for the conversion of alicyclic ketones into unsaturated aldehydes Expired GB392062A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH392062X 1931-10-30

Publications (1)

Publication Number Publication Date
GB392062A true GB392062A (en) 1933-05-11

Family

ID=4513966

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27932/32A Expired GB392062A (en) 1931-10-30 1932-10-07 An improved process for the conversion of alicyclic ketones into unsaturated aldehydes

Country Status (1)

Country Link
GB (1) GB392062A (en)

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