A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone
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 suitab...
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| Veröffentlicht in: | Journal of chemical education 2005-12, Vol.82 (12), p.1837 |
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| creator | Esteb, John J Hohman, J. Nathan Schlamadinger, Diana E Wilson, Anne M |
| description | 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. |
| doi_str_mv | 10.1021/ed082p1837 |
| format | Article |
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| ispartof | Journal of chemical education, 2005-12, Vol.82 (12), p.1837 |
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| source | American Chemical Society Journals |
| subjects | Chemical reactions Chemistry College students Design of experiments Esters Ketones Laboratory Experiments Lactones Methods Research Molecular Structure Organic chemistry Scientific Methodology Solvents Students Synthesis Undergraduate Study |
| title | A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone |
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