Green Oxidation of Ketones to Lactones with Oxone in Water

J Org Chem. 2021 Nov 5;86(21):15712-15716. doi: 10.1021/acs.joc.1c01469. Epub 2021 Oct 13.

Abstract

Cyclic ketones were quickly and quantitatively converted to 5-, 6-, and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and nonpollutant oxidizing reagent, in 1 M NaH2PO4/Na2HPO4 water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed, thus making the adoption of more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis unnecessary. With some changes, the method was successfully applied also to water-insoluble ketones such as adamantanone, acetophenone, 2-indanone, and the challenging cycloheptanone.

MeSH terms

  • Ketones*
  • Lactones
  • Oxidation-Reduction
  • Sulfuric Acids
  • Water*

Substances

  • Ketones
  • Lactones
  • Sulfuric Acids
  • Water
  • potassium peroxymonosulfuric acid