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Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate

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Gayle J. Pageau , Rodwell Mabaera , Kathryn M. Kosuda , Tamara A. Sebelius , Ali H. Ghaffari , Kenneth A. Kearns , Jean P. McIntyre , Tina M. Beachy and Dasan M. Thamattoor

Department of Chemistry, Colby College, Waterville, ME 04901

J. Chem. Educ., 2002, 79 (1), p 96

DOI: 10.1021/ed079p96

Publication Date (Web): January 1, 2002

Section:

History, Education, and Documentation

Abstract

The diastereoselective synthesis of ethyl (E)-3-methyl-3-phenylglycidate, a strawberry flavoring agent, is carried out by epoxidizing ethyl trans-β-methylcinnamate with m-chloroperbenzoic acid. This epoxidation is appropriate for the introductory organic laboratory and augments the small number of such experiments currently available for undergraduate education. In the course of performing this exercise, students are exposed to many important facets of organic chemistry such as synthesis, reaction mechanism, stereochemistry, chromatography, quantitative analysis, spectroscopy, and computational chemistry. The ¹H NMR spectrum of this compound is especially interesting and presents instructive examples of diastereotopic protons and shielding effects of the aromatic ring current.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Inquiry-Based / Discovery Learning

Keywords (Subject):

Molecular Modeling

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