Direct esterification of fatty acids with phenylalkanols by using dicyclohexylcarbodiimide

Abstract

A mild one-pot esterification method of fatty acids with alcohols at room temperature is described. The reaction of undec-10-enoic acid (I) with 1-phenylethanol in the presence of N,N′-di-cyclohexylcarbodiimide and 4-(N,N-dimethylamino)pyridine gave 1′-phenylethyl undec-10-enoate in quantitative yield. Similar reactions were also carried out with (Z)-octadec-9-enoic acid, (Z)-12-hydroxyoctadec-9-enoic and (Z)-9- hydroxyoctadec-12-enoic acids. In addition, compound (I) was allowed to react with diphenyl methanol to form its corresponding ester. The structure elucidation of the prepared esters is based on the elemental analysis and spectral data (IR, 1H- and 13C-NMR, MS).