Hydrochloric Acid → CHOL-5-EN-24-oic acid, 3-hydroxy-, methyl ester, (3beta)-

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Reaction Steps

60.1 g of the crude 3β-acetoxy-5-cholenic acid methyl ester was refluxed with a solution of 56.0 g of potassium hydroxide in 1.35 liters of methanol for two hours. The solution was cooled to room temperature and poured into 500 ml of 10% hydrochloric acid. The precipitate was isolated by filtration, washed with water and dried. The crude 3β-hydroxy-5-cholenic acid weighed 50.1 g. Of this, 20.3 g was refluxed for 22 hours with 2 liters of methanol containing 1 g of p-toluenesulfonic acid. The solvent was removed by distillation, the residue dissolved in ether, washed with dilute alkali and water, and the solvent evaporated. 20.3 g of 3β-hydroxy-5-cholenic acid methyl ester was obtained. On recrystallization from heptane the mp was 144°-145° C. Anal. Calcd for C25H40O3 : C, 77.27; H, 10.38. Found: C, 77.04; H, 10.01.

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