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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > November  >
In the Laboratory
The Synthesis of a Cockroach Pheromone
An Experiment for the Second-Year Organic Chemistry Laboratory
Patty L. Feist
Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309
Cover
November 2008
Vol. 85 No. 11
p. 1548

Abstract
This experiment describes the synthesis of gentisyl quinone isovalerate, or blattellaquinone, a sex pheromone of the German cockroach that was isolated and identified in 2005. The synthesis is appropriate for the second semester of a second-year organic chemistry laboratory course. It can be completed in two, three-hour laboratory periods and uses equipment readily available in most organic chemistry laboratories. In the first step, 2,5-dimethoxybenzyl alcohol reacts with isovaleryl chloride to produce 2,5-dimethoxybenzyl 3-methylbutanoate. In the second step, the 2,5-dimethoxybenzyl 3-methylbutanoate is oxidized using ceric ammonium nitrate to form gentisyl quinone isovalerate. The experiment is interesting to students because it involves the synthesis of a compound that has real-world applications. The experiment affords them practice in the important techniques of extraction, IR spectroscopy, and NMR spectroscopy.

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Supplement
Notes for the instructor; Student version of the experiment; IR and NMR spectra of the intermediate and product
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Contents
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Citation
Feist, Patty L. J. Chem. Educ. 2008, 85, 1548.
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Keywords
Esters; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Natural Products; NMR Spectroscopy; Organic Chemistry; Oxidation / Reduction; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
9/19/2008
9/25/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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