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A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone
Journal of Chemical Education (2005)
  • John J. Esteb, Butler University
  • James N. Hohman
  • Diana E. Schlamadinger
  • Anne M. Wilson
Abstract

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.

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Disciplines
Publication Date
2005
Citation Information
John J. Esteb, James N. Hohman, Diana E. Schlamadinger and Anne M. Wilson. "A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone" Journal of Chemical Education Vol. 82 Iss. 12 (2005)
Available at: http://works.bepress.com/john_esteb/6/