THE SYNTHESIS OF 2-KETOCYCLOHEXYLSUCCINIC ACID AND RELATED SUBSTANCES: I. SYNTHESES INVOLVING CYCLOHEXENE OXIDE
- 1 January 1943
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Research
- Vol. 21b (1) , 1-12
- https://doi.org/10.1139/cjr43b-001
Abstract
A synthesis of 2-ketocyclohexylsuccinic acid is described. This substance has been prepared by the oxidation of the γ-lactone of cyclohexanolsuccinic acid, which results from the condensation of cyclohexene oxide, the sodio-derivative of malonic ester, and ethyl bromoacetate, followed by hydrolysis and decarboxylation. The lactone of the keto acid and the lactam formed when the keto acid is treated with alcoholic ammonia are described. 2-Ketocyclohexylacetic and 2-ketocyclohexylmalonic acids have also been prepared. Alkyl halides may be substituted for ethyl bromoacetate in the above reaction. Methyl iodide yields the γ-lactone of cyclohexanol-α-propionic acid and benzyl chloride the γ-lactone of cyclohexanol-α-benzylacetic acid. Oxidation of these lactones with bromine and magnesium hydroxide yields 2-ketocyclohexyl-α-propionic acid and 2-ketocyclohexylbenzylacetic acid.Keywords
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