Palmitic Acid → 2-Hydroxydecanoic Acid

Participants

Reaction Steps

2-Bromohexadecanoic acid (m.p. 51.5°-52.5° C) prepared from palmitic acid of high purity according to the method of Schwenk, E. and Papa, D; J. Am. Chem. Soc., 70 (1948) 3626, was treated with a solution of potassium hydroxide in 95 % methanol in an oil bath at 90° C at which 2-hydroxyhexadecanoic acid (m.p. 86.1°-86.3° C after recrystallization from ethanol and then from dichloromethane) was formed. Methyl 2-methoxyhexadecanoate (m.p. 28.6°-30.6° C) was obtained from 2-hydroxydecanoic acid by esterification and etherification with diazomethane using borone trifluoride as catalyst for the esterification whereafter it was reduced with lithium aluminum hydride to the formation of 2-methoxyhexadecanol-1 (m.p. 34.3°-34.9° C) which was purified by chromatography on silicic acid, 2-methoxyhexadecyl p-toluenesulphonate (m.p. 38°-39° C) was prepared by treating 2-methoxyhexadecanol with p-toluenesulphonylchloride in pyridine.

Provenance & Evidence