Synthesis of 2-Acetylthiophene by the Acylation of Thiophene Using Acetic Anhydride and Iodine (A Revisiting after Almost Sixty Years)

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 9 Issue 3 (2004) pp 163-165

Synthesis of 2-Acetylthiophene by the Acylation of Thiophene Using Acetic Anhydride and Iodine (A Revisiting after Almost Sixty Years)

Donald C. Bowman

Department of Science, Math, and Engineering, Central Virginia Community College, Lynchburg, VA 24502; bowmand@cvcc.vccs.edu
Received March 4, 2004. Accepted April 6, 2004.

Published online: 30 April 2004

Abstract. Herein is described an experimental procedure for an electrophilic aromatic substitution utilizing a heterocyclic substrate instead of the more commonly used benzenoid substrates. Thiophene is acetylated under mild conditions using acetic anhydride and iodine. This method was reported almost sixty years ago as part of a series of thiophene acetylation experiments involving various acetylating agents and various Lewis acid catalysts. A report on the spectra of the product (not given in the original work) is now included, as well as an alternative final distillation and purification procedure. While not originally conceived as a college laboratory exercise, this experiment is excellent for those wanting to include heterocyclic chemistry in their laboratory course.

Key Words: Laboratories and Demonstrations; organic chemistry; heterocyclic chemistry; synthesis

(*) Corresponding author. (E-mail: bowmand@cvcc.vccs.edu)

Article in PDF format (215 KB) HTML format

Supporting Materials: