A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone

Document Type


Publication Date

January 2005

Publication Title

Journal of Chemical Education


We present an experiment involving the Baeyer–Villiger oxidation reactionfor a first-year organic chemistry class. The Baeyer–Villiger reactionprovides an efficient method to convert ketones to esters or lactones. Most organictextbooks cover the Baeyer–Villiger reaction but owing to a lack of suitableexperiments, students seldom get to explore the reaction in the undergraduateteaching laboratory. In this experiment, m-chloroperoxybenzoic acid(m-CPBA) and4-tert-butylcyclohexanone are mixed together for 30 minutes under solvent-freeconditions to produce γ-t-butyl-ε-caprolactone in 95%yield. The solvent-free nature of this procedure greatly limits the quantityof waste generated by students and keeps costs low by removing the need for solvent. Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information will be required for access. Users not affiliated with Butler University should contact their local librarian for assistance in locating a copy of this article.