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  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > March  >
In the Laboratory
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets
Ryan G. Stabile and Andrew P. Dicks
Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6
Cover
March 2003
Vol. 80 No. 3
p. 313
Abstract
The synthesis of racemic 3-(2-methoxyphenoxy)-1,2-propanediol (guaifenesin), an expectorant found in well-known cough syrups such as Benylin, is undertaken by a Williamson ether synthesis reaction. The same compound is simultaneously isolated and characterized from commercially available Guai-Aid cough tablets. The experiment is well-suited towards the introductory part of an advanced organic laboratory course and complements typical lecture topics in a stimulating manner. Consideration is given towards reaction mechanisms, stereochemistry, optical activity, pharmaceutical synthesis, and spectroscopic analysis. Discussion of the merits or disadvantages of marketing a drug as a racemic mixture, with reference to the notorious thalidomide case study, and the concept of enantioselective synthesis is possible.

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*  Citation
 Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003 80 313.
*  Keywords
 Chirality / Optical Isomers; Drugs / Pharmaceuticals; Laboratory Instruction; Mechanisms; Microscale; Organic Chemistry; Organic Synthesis; Stereochemistry
*  History
 Created:
Last Updated:		 February 6, 2003
February 28, 2005
Link to Featured Molecules added (April 2004).
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