Green Oxidation of Ketones to Lactones with Oxone in Water

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.

Automated summary

Treatment of cyclic ketones with Oxone in 1M NaH2PO4/Na2HPO4 water solution can efficiently and quantitatively convert them into 5-, 6-, and 7-membered lactones, important synthons, without the formation of hydroxyacids. This green and simple method eliminates the need for more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis, and can also be applied to water-insoluble ketones.