Chemoselective Reactions of Citral: Green Syntheses of Natural Perfumes for the Undergraduate Organic Laboratory
Chemoselectivity is a central concept in organic synthesis and may be readily appreciated in the context of the fragrant, polyfunctional natural product citral. We describe three single-step reactions students may perform on citral to synthesize other natural perfumes: citronellal, geraniol, nerol, or epoxycitral. Each of the reactions uses a simple catalyst and results in a crude product that may be analyzed directly. Hazards and waste are kept to a minimum. Product characterization may include thin-layer chromatography, NMR and IR spectroscopy, GC−MS, and smell. These reactions are chemoselective, biomimetic, and illustrate several principles of green chemistry.
© 2010 The American Chemical Society and Division of Chemical Education, Inc.
“Chemoselective reactions of citral: Green syntheses of natural perfumes for the undergraduate organic laboratory,” Cunningham, A.D.*; Ham, E.Y.*; Vosburg, D.A. J. Chem. Educ. 2011, 88, 322-324. DOI: 10.1021/ed100539m