Abstract
Several procedures are evaluated for synthesis of phosphorus-containing derivatives of some long-chain hydroxy-fatty acids, including ricinoleic and lesquerolic acid and their hydrogenated products. The conventional method of preparing phosphate esters by reaction of an alcohol with a dialkyl phosphorochloridate is unsatisfactory, but introduction of the dialkyl phosphoryl group was accomplished by using dimethylformamide as catalyst. Phosphorus derivatives are obtained more conveniently by ester interchange between a long-chain hydroxy compound and a low molecular weight dialkyl phosphite. Purification of the phosphite esters was accomplished by partitoning between acetonitrile and petroleum ether and also by chromatography on a column of silicic acid. Attempts to prepare phosphorus derivatives of the allylic hydroxyl of methyl dimorphecolate resulted in extensive dehydration to the conjugated triene.
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A laboratory of the W. Utiliz. Res. & Dev. Div., ARS, U.S.D.A.
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Diamond, M.J., Applewhite, T.H., Knowles, R.E. et al. Preparation of phosphorus esters of long-chain hydroxy fatty acids. J Am Oil Chem Soc 41, 9–13 (1964). https://doi.org/10.1007/BF02661892
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DOI: https://doi.org/10.1007/BF02661892