Featured Molecules: Enantiomers of Guaifenesin

In the Laboratory edited by

JCE WebWare

William F. Coleman Wellesley College Wellesley, MA 02481

Featured Molecules: Enantiomers of Guaifenesin

Randall J. Wildman University of Wisconsin–Madison Madison, WI 53715

March Featured Molecules The WebWare molecules of the month for March are the enantiomers of guaifenesin. The synthesis of the guaifenesin racemate and of the enantiomers is described in the paper by Stabile and Dicks, “Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets” on p 313. Guaifenesin [3-(2-methoxyphenoxy)-1,2-propanediol] is used as an expectorant in a number of commercially available cough medicines. Fully manipulable (Chime) versions of these and other molecules are available at the Only@JCE Online Web site: http:// jchemed.chem.wisc.edu/JCEWWW/Features/WebWare/ MonthlyMolecules/2003/Mar/.

(S)-(+)-guaifenesin

(R)-(−)-guaifenesin

JCE WebWare http://jchemed.chem.wisc.edu/jcewww/Features/Webware JChemEd.chem.wisc.edu • Vol. 80 No. 3 March 2003 • Journal of Chemical Education

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