Sodium Hydroxide → (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of (E)-3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester (5.7 g, 17.95 mmol) in ethanol (65 mL) was treated with a 1N aqueous sodium hydroxide solution (54 mL). The solution was heated at 45-50° C. for 15 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (100 mL) and extracted with diethyl ether (1×150 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×250 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid (5.18 g, 94%) as a white solid: mp 195-197° C.; EI-HRMS m/e calcd for C16H20O4S (M+H)+309.1160, found 309.1165.

Provenance & Evidence