Expeditious Horner-Wadsworth–Emmons Synthesis of Methyl Cinnamate Esters under Aqueous Conditions

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 10 Issue 4 (2005) pp 300-302

Expeditious Horner-Wadsworth–Emmons Synthesis of Methyl Cinnamate Esters under Aqueous Conditions

Lawrence L. W. Cheung, Rui Jun Lin, Jason W. McIntee, and Andrew P. Dicks*

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6, adicks@chem.utoronto.ca
Received June 7, 2005. Accepted June 27, 2005.

Published online: 6 July 2005

Abstract. The rapid and facile preparation of methyl (E)-cinnamate esters by a Horner–Wadsworth–Emmons reaction is detailed. Reactions are undertaken using environmentally benign potassium carbonate as a base in an aqueous medium. This methodology introduces a significant reduction in reaction time compared to previous undergraduate experiments. An occasion exists to promote recognition of the role water plays as a solvent for organic reactions and aspects of green chemistry.

Key Words: Laboratories and Demonstrations; organic chemistry; microscale synthesis; aqueous reactivity; Horner–Wadsworth–Emmons reaction; methyl cinnamate esters

(*) Corresponding author. (E-mail: adicks@chem.utoronto.ca)

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Supporting Materials:

Laboratory notes for students (including experimental procedures and postlaboratory questions), additional notes for instructors, and product spectroscopic information (NMR, IR, MS and UV spectra and assignments) are available in a Zip file. (373 KB)