A Simple, Rapid Microwave-Based Procedure for the Synthesis of O-Methylated and N,O-Dimethylated Derivatives of Hydroxamic Acids Suitable for the Undergraduate Laboratory

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 24 (2019) pp 80-83

A Simple, Rapid Microwave-Based Procedure for the Synthesis of O-Methylated and N,O-Dimethylated Derivatives of Hydroxamic Acids Suitable for the Undergraduate Laboratory

Carolina Durand, Tiauna Griffin-Blake, Haylie Shinsato and Robert Aslanian*

Department of Chemistry, New Jersey City University, Jersey City, NJ 07305, raslanian@njcu.edu
Received February 5, 2019. Accepted March 13, 2019.

Published: 2 May 2019

Abstract. Hydroxamic acids and their alkylated derivatives are important functional groups in many natural products and drugs as well as important synthetic intermediates for the preparation of ketones. They are typically formed by an acyl substitution reaction, a fundamental reaction in organic chemistry that is taught as part of the organic curriculum. Although there are numerous procedures for their preparation, many take a significant amount of time for the reaction to reach completion or utilize very reactive reagents, which makes them unsuitable for use in an undergraduate lab setting. We have modified a literature procedure to give a safe, rapid method for the preparation of the N,O-dimethylated and O-methylated derivatives using carbonyl diimidazole. We have successfully employed this procedure in our organic II lab.

Key Words: Laboratories and Demonstrations; organic chemistry; acyl substitution; hydroxamic acid analogs; microwave-assisted reaction

(*) Corresponding author. (E-mail: raslanian@njcu.edu )

Article in PDF format (406 KB) HTML format