Multi-Week Synthesis of a Sunscreen Agent for the Organic Chemistry Laboratory

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 9 Issue 1 (2004) pp 27-29

Multi-Week Synthesis of a Sunscreen Agent for the Organic Chemistry Laboratory

Gary W. Breton* and Melanie K. Belk

Berry College, Department of Chemistry, PO Box 495016, Mount Berry, GA 30149, gbreton@berry.edu
Received November 4, 2003. Accepted November 28, 2003.

Published online: 22 January 2004

Abstract. A multi-week laboratory experiment on the synthesis of the sunscreen agent octyl 4-methoxycinnamate is presented. The synthesis of the compound illustrates the usefulness of three important synthetic methods typically encountered in the second semester of a traditional organic chemistry course. Reasonable-to-good average yields were obtained for each of the synthetic steps by our organic chemistry laboratory students. The effectiveness of the synthesized sunscreen was evaluated utilizing UV–vis spectroscopy.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: gbreton@berry.edu)

Article in PDF format (219 KB) HTML format

Supporting Materials:

Experimental procedure for the synthesis of the intermediate, methyl methoxycinnamate (2), a student handout for the laboratory experiment, and copies of relevant ¹H NMR spectra are available in a Zip file (458 KB).