The Synthesis of a Cockroach Pheromone. An Experiment for the Second-Year Organic Chemistry Laboratory.

• Autores: Patty L. Feist
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 85, Nº 11, 2008, págs. 1548-1549
• Idioma: inglés
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• Resumen

  • 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.