A Multi-Step Synthesis of Triphenylmethanol

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 9 Issue 6 (2004) pp 370-373

A Multi-Step Synthesis of Triphenylmethanol

Shelly B. Blunt* and Victor F. Hoffman

Department of Chemistry, University of Southern Indiana, Evansville, IN 47712, sblunt@usi.edu and Department of Chemistry, Truman State University, Kirksville, MO 63501, vhoffman@truman.edu
Received August 4, 2004. Accepted September 15, 2004.

Published online: 6 October 2004

Abstract. This laboratory experiment combines simple one-step reactions into a capstone experience for the undergraduate organic chemistry laboratory. An environmentally benign haloform oxidation of acetophenone to benzoic acid begins this multi-step sequence. Yields of a Fischer esterification of benzoic acid to methyl benzoate are optimized with a modified Dean-Stark trap. Lastly, the methyl benzoate is converted through a classical Grignard reaction into triphenylmethanol. This sequence utilizes many of the techniques and skills learned throughout the organic chemistry laboratory curriculum and offers improvements in yields of the reactions. Additionally, the experiment allows for discussion of “green” chemistry techniques and reinforces several concepts presented in the lecture portion of the course.

Key Words: Laboratories and Demonstrations; organic chemistry; haloform oxidation; fischer esterification; grignard

(*) Corresponding author. (E-mail: sblunt@usi.edu)

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