Standard methods for the identification of alcohols often produce questionable results. The infrared spectrum of a 3 5-dinitrobenzoate ester permits rapid identification of the original alcohol. Therefore, reference infrared spectra have been obtained for the 3,5-dinitrobenzoate derivatives of 24 alcohols containing from 1 to 22 carbon atoms. The infrared spectra of these 3,5-dinitrobenzoate derivatives are unique; even closely related alcohols that differ only by one methylene group form 3,5-dinitrobenzoate esters, which often exhibit markedly different infrared spectra. Although the melting points of these derivatives may be close, the infrared spectra permit positive identification. In qualitative analysis, infrared techniques can be used either alone or in conjunction with x-ray diffraction techniques.
Robert C. Douthit, Kenneth J. Garska, and Victor A. Yarborough, "Characterization of Hydroxyl Compounds Identification of Their 3,5-Dinitrobenzoate Esters by Infrared Spectroscopy," Appl. Spectrosc. 17, 85-89 (1963)