Oxidation of Benzoylacetones with Peracetic Acid in Acetic Acid

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  • FURUYA Yoshiaki
    Department of Industrial Chemistry, Faculty of Engineering, Kumamoto University
  • ITOHO Kazuo
    Daiichi College of Pharmaceutical Sciences

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Other Title
  • 酢酸中でのベンゾイルアセトンの過酢酸酸化

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Description

The oxidation of benzoylacetone (abbreviated as BA) and its derivatives with peracetic acid has been followed iodometrically. The initial rate of the consumption of peracetic acid satisfied the following equation: Rate = { k2 + k3 C H2SO4}CBA CAcO2H The first and second terms represent the non and the acid-catalyzed oxidation, respectively. The plots of log k2 vs. (σ+ 1.00 Δr+) and log ks vs. σ gave straight lines with slopes of -0.79and -0.85, respectively. The formation of several materials containing acids, aldehydes a n d an ester such as benzoic, pyruvic, benzoylformic acids, carbon dioxide, benzaldehyde, phenylglyoxal, and acetonyl benzoate were confirmed by means of GC and/or TLC. From these results, a probable mechanism which involves an epoxidation by an attack of the positive oxygen atom of peracetic acid on BA and protonated peracetic acid on BA was postulated and discussed. In this oxidation, Baeyer-Villiger reaction would take place slightly as a side reaction giving acetonyl benzoate. In addition, it was confirmed that H atom (or alkyl group) on active methylene of BA (or alkyl-substituted BA) did not migrate in our reaction condition.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1976 (7), 1088-1092, 1976-07-10

    The Chemical Society of Japan

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