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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > December  >
In the Laboratory
A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ- t-Butyl-ε-caprolactone
John J. Esteb, J. Nathan Hohman, Diana E. Schlamadinger, and Anne M. Wilson
Clowes Department of Chemistry, Butler University, Indianapolis, IN 46208
Cover
December 2005
Vol. 82 No. 12
p. 1837
Abstract
We present an experiment involving the Baeyer–Villiger oxidation reaction for a first-year organic chemistry class. The Baeyer–Villiger reaction provides an efficient method to convert ketones to esters or lactones. Most organic textbooks cover the Baeyer–Villiger reaction but owing to a lack of suitable experiments, students seldom get to explore the reaction in the undergraduate teaching laboratory. In this experiment, m-chloroperoxybenzoic acid (m-CPBA) and 4-tert-butylcyclohexanone are mixed together for 30 minutes under solvent-free conditions to produce γ-t-butyl-ε-caprolactone in 95% yield. The solvent-free nature of this procedure greatly limits the quantity of waste generated by students and keeps costs low by removing the need for solvent.
Supplement
Instructions for the students and notes for the instructor are available.
*  Contents JCE2005p1837W.doc (Microsoft Word)
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*  Citation
 Esteb, John J.; Hohman, J. Nathan; Schlamadinger, Diana E.; Wilson, Anne M. J. Chem. Educ. 2005 82 1837.
*  Keywords
 Esters; Green Chemistry; Hands-On Learning / Manipulatives; Laboratory Instruction; Organic Chemistry; Oxidation / Reduction; Second-Year Undergraduate; Synthesis
*  History
 Created:
Last Updated:		 October 25, 2005
November 4, 2005
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