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

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

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 s...

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Veröffentlicht in:Journal of chemical education 2002-01, Vol.79 (1), p.96
Hauptverfasser: Pageau, Gayle J, Mabaera, Rodwell, Kosuda, Kathryn M, Sebelius, Tamara A, Ghaffari, Ali H, Kearns, Kenneth A, McIntyre, Jean P, Beachy, Tina M, Thamattoor, Dasan M
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container_issue 1
container_start_page 96
container_title Journal of chemical education
container_volume 79
creator Pageau, Gayle J
Mabaera, Rodwell
Kosuda, Kathryn M
Sebelius, Tamara A
Ghaffari, Ali H
Kearns, Kenneth A
McIntyre, Jean P
Beachy, Tina M
Thamattoor, Dasan M
description 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.
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title Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate
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