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A Modified Synthesis of the Insect Repellent DEET

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Peter H. Knoess and Edward G. Neeland

Okanagan University-College, Dept. of Chemistry, 3333 College Way, Kelowna, British Columbia V1V 1V7, CANADA

J. Chem. Educ., 1998, 75 (10), p 1267

DOI: 10.1021/ed075p1267

Publication Date (Web): October 1, 1998

Section:

History, Education, and Documentation

Abstract

In the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET. In our students' hands, these procedures gave a darkly colored product which was contaminated with an anhydride by-product. We have shown that the m-toluoyl chloride can be prepared at room temperature in 8 minutes and that the eventual DEET product is obtained in excellent yield without the dark coloration or anhydride by-product.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Synthesis of N,N-Diethyl-3-methylbenzamide (DEET): Two Ways to the Same Goal
Jean Christophe Habeck, Lamine Diop and Michael Dickman
Journal of Chemical Education2010 87 (5), 528-529
- Synthesis of N,N-Diethyl-3-methylbenzamide (DEET): Two Ways to the Same Goal
  Jean Christophe Habeck, Lamine Diop and Michael Dickman
  Journal of Chemical Education2010 87 (5), 528-529
  A dimethyl formamide-catalyzed synthesis of N,N-diethyl-3-methylbenzamide (DEET) from toluic acid and oxalyl chloride in an introductory organic chemistry laboratory course is presented. Students use this procedure and another procedure previously ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment
Victor Cesare , Ishwar Sadarangani , Janet Rollins and Dennis Costello
Journal of Chemical Education2004 81 (5), 713
- The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment
  Victor Cesare , Ishwar Sadarangani , Janet Rollins and Dennis Costello
  Journal of Chemical Education2004 81 (5), 713
  This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic ...
  Abstract | Hi-Res PDF | PDF w/ Links
An Indexed Combinatorial Library: The Synthesis and Testing of Insect Repellents
William H. Miles , Kathy A. Gelato , Kristen M. Pompizzi , Aislinn M. Scarbinsky and Brian K. Albrecht , Elaine R. Reynolds
Journal of Chemical Education2001 78 (4), 540
- An Indexed Combinatorial Library: The Synthesis and Testing of Insect Repellents
  William H. Miles , Kathy A. Gelato , Kristen M. Pompizzi , Aislinn M. Scarbinsky and Brian K. Albrecht , Elaine R. Reynolds
  Journal of Chemical Education2001 78 (4), 540
  An indexed combinatorial library of amides was prepared by the reaction of amines and acid chlorides. A simple test for insect repellency using fruit flies (Drosophila melanogaster) allowed the determination of the most repellent sublibraries. The student-...
  Abstract | Hi-Res PDF | PDF w/ Links