Contact Information

Author
  • Andy Dicks
  • Senior Lecturer
  • Chemistry
  • Univ. of Toronto
  • 80 St. George Street
  • Toronto, ON
  • M5S 3H6
  • Canada
Email
Phone
(416) 946 - 8003
Website

A Microscale Heck Reaction In Water

Laboratory Procedure (PDF)

Author Contact: adicks@chem.utoronto.ca

Summary

This laboratory experiment features the palladium-catalyzed Heck synthesis of (E)-4-acetylcinnamic acid from 4-iodoacetophenone and acrylic acid by mid-level undergraduates. Traditional Heck reaction organic solvents (e.g. acetonitrile) and base (e.g. triethylamine) are replaced by water and sodium carbonate respectively. This approach introduces fundamentals of green chemistry (aqueous and catalytic reactivity) to students whilst highlighting contemporary research via an industrially important reaction.

Supplemental materials include (a) laboratory notes for students, (b) additional notes for instructors, and (c) spectroscopic information and physical data.

Summary prepared July 2008 by Andrew P. Dicks, Department of Chemistry at the University of Toronto.

Source

Cheung, L.; Aktoudianakis, E.; Chan, E.; Edward, A. R.; Jarosz, I.; Lee, V.; Mui, L.; Thatipamala, S. S.; Dicks, A. P. Chem. Educator [Online], Online 2007, 12, pp 77-79.

Chem. Educator [Online] Abstract

Category Descriptors

Chemistry Concepts
  • Alkenes
  • Aqueous Solution Chemistry
  • Catalysis
  • Organometallics
  • Stereochemistry
Laboratory Techniques
  • Assembly of Reaction Apparatus
  • IR Spectroscopy
  • Melting Points and Melting Ranges
  • Microscale Lab
  • NMR Spectroscopy
  • Recrystallization
Green Chemistry Principles
  • Design Less Hazardous Chemical Syntheses
  • Use Catalysts
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles