Abstract and Summary
9(10)-Formylstearic acid and methyl 9(10)-formylstearate reacted with formaldehyde in basic methanolic or aqueous medium to undergo the Tollens condensation, followed by a crossed Cannizzaro reaction to give 9,9(10,10)-bis(hydroxymethyl)-octadecanoic acid in essentially quantitative yield. This 2,2-disubstituted-1,3-propanediol has been esterified on the carboxyl group and the hydroxymethyl groups have been acetylated and acetalated with acetone to give a series of stable liquids boiling at ca. 200 C/0.005 mm and freezing at <−70 C.
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Miller, W.R., Pryde, E.H. Germinal hydroxymethyl compounds from 9(10)-formylstearic acid. J Amer Oil Chem Soc 54, A882–A885 (1977). https://doi.org/10.1007/BF02909060
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DOI: https://doi.org/10.1007/BF02909060