Preparation of 1-phenyl alkyl esters of medium and long-chain fatty acids

Abstract

Two sets of 1-phenyl alkyl ester derivatives were synthesized from the acyl chlorides of medium- and long-chain fatty acids and 1-phenyl-1-alkanols. The 1H-NMR analysis of these ester derivatives gave a characteristic signal at 5.73—5.89 δ for the methine proton (— COOC HPhR , where R = alkyl). The 13C-NMR analysis was very informative, permitting the identification of the ortho-, meta-, para- and substituted carbon nuclei of the aromatic system. The effects of the ester linkage (—COO—) and the phenyl group on the neighboring carbon atoms in the ester fraction of these molecules provided detail structural information to characterize these ester derivatives. From the mass spectral fragmentation pattern, the position of the ester linkage and the position of the phenyl group could be readily determined in addition to the chain lengths in the alkyl or ester fraction of these compounds. The thin-layer and gas-liquid chromatographic properties and the infrared spectroscopic behavior of these derivatives were also examined.