Green Oxidation of Ketones to Lactones with Oxone in Water

Valentina Bertolini, Rebecca Appiani, Marco Pallavicini and Cristiano Bolchi*

*Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy, Email: cristiano.bolchiunimi.it

V. Bertolini, R. Appiani, M. Pallavicini, C. Bolchi, J. Org. Chem., 2021, 86, 15712-15716.

DOI: 10.1021/acs.joc.1c01469

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Abstract

Cyclic ketones were quickly and quantitatively converted to 5-, 6-, and 7-membered lactones by treatment with Oxone, a cheap, stable, and nonpollutant oxidizing reagent in 1 M NaH₂PO₄/Na₂HPO₄ water solution (pH 7). These simple and green conditions avoid the formation of hydroxyacid. With some changes, the method can also be applied to water-insoluble ketones.

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Key Words

Baeyer-Villiger Oxidation, Lactones, Oxone, Green Chemistry

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ID: J42-Y2021