Sodium Hydroxide → 8-Acetyl-8-phenyl-12-benzyloxyheptadecanoic acid

Participants

Reaction Steps

A mixture of ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate (14 g., crude), sodium hydroxide (2.0 g., 0.05 mole) and methanol (150 ml.) is stirred for 48 hours. The methanol is removed in vacuo; and the residual oil is poured into H2 0 (100 ml.), acidified with 6 N HCl (100 ml.), extracted with ether, and the combined ether extracts dried over anhydrous Na2SO4. The ether is removed in vacuo, and the residual oil is chromatographed through a silica gel column (95% CHCH3 -5% MeOH) to obtain 8-acetyl-8-phenyl-12-benzyloxyheptadecanoic acid (1.43 g., slightly impure).

Provenance & Evidence