The Reduction of Some Phthalamic Acids with Lithium Aluminum Hydride

The phthalamic acids II and VII derived from 2-phthalimidooctadecane (I) and (-)-2-phthalimido-3-octadecanone (VI) were submitted to reduction with lithium aluminum hydride. The reduction of II afforded two products, i. e. 2-(o-hydroxymethylbenzamido)-octadecane (III) and 2-(o-hydroxymethylbenzylamino)-octadecane(IV). By reduction of VII only 2-(o-hydroxymethylbenzamido)-3-octadecanol (VIII) was obtained. When hydrolyzed III and VIII yielded, after subsequent acylation, 2-acetamidooctadecane (V) and 2-benzami do-3-hydroxyoctadecane (IX), respectively. The hydrogenolysis of IV afforded V. These reactions may present an alternative method for the elimination of the phthaloyl group