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Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog

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Ryan G. Stabile and Andrew P. Dicks

Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada

J. Chem. Educ., 2004, 81 (10), p 1488

DOI: 10.1021/ed081p1488

Publication Date (Web): October 1, 2004

Section:

History, Education, and Documentation

Abstract

The two-step synthesis and characterization of a sunscreen analog (ethyl trans-4-methoxycinnamate) is presented. This experiment is tailored towards students with a sound theoretical understanding of organic chemistry and related laboratory techniques. Appropriate synthetic discussion topics include carbonyl condensation reactions, carboxylic acid esterifications, and the so-called "cesium effect" in organic synthesis. Product geometry may be concealed and deduced by spectroscopic analysis. The product ¹H NMR spectrum reinforces classical concepts of electronic shielding–deshielding effects and proton coupling. Students are able to connect the structure of ethyl trans-4-methoxycinnamate with its ability to act as an ultraviolet light absorber.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Conductivity

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