Abstract
Methyl tetracosanate and methyl hexacosanate were each reacted in xylene, in the presence of sodium hydride and respectively formed methyl 2-docosyl-3-oxo-hexacosanate (I) and methyl 2-tetracosyl-3-oxoöctacosanate (I′), each in good yield. Each was reduced with sodium borohydride, saponified, and purified by chromatography, respectively affording 2-docosyl-3-hydroxyhexacosanoic acid (IIIα), m.p. 91-92.5°, (IIIβ), m.p. 86-88°, and 2-tetracosyl-3-hydroxyoctacosanoic acid (III′α), m.p. 92-93.5°, and (III′β), m.p. 87-89°. These compounds were identified by infrared spectra and through their acetates. 2-Docosylhexacosane-1, 3-diol (IV), m.p. 75.5-77°, and 2-tetracosyloctacosane-1, 3-diol (IV′), m.p. 78-79.5°, were isolated as the by-products of (III) and (III′). On the other hand, saponification of (I) and (I′) respectively afforded lignocerone (II) and cerotone (II′), which were identified by their oximes.
