This experiment features the rapid and straightforward preparation of a sunscreen analog by a Horner-Wadsworth-Emmons reaction in water. Performed at the mid-undergraduate level, students use environmentally benign potassium carbonate as a base in an aqueous medium to synthesize and purify cinnamate esters. This strategy introduces a significant reduction in reaction time compared to previous pedagogical experiments, facilitates recognition of the role water plays as a solvent for organic reactions and provides a springboard for discussion of other green chemistry principles.
Summary prepared July 2008 by Andrew P. Dicks, Department of Chemistry at the University of Toronto.
Cheung, L.; Lin, R. J.; McIntee, J. W.; Dicks, A. P. Chem. Educator [Online], Online 2005, 10, pp 300-302.