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A Solvent-Free Baeyer–Villiger Lactonization For The Undergraduate Organic Laboratory: Synthesis Of Γ-T-Butyl-Ε-Caprolactone, John Esteb, James Hohman, Diana Schlamadinger, Anne Wilson
A Solvent-Free Baeyer–Villiger Lactonization For The Undergraduate Organic Laboratory: Synthesis Of Γ-T-Butyl-Ε-Caprolactone, John Esteb, James Hohman, Diana Schlamadinger, Anne Wilson
John Esteb
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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