Sodium Hydroxide → (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)methylene]succinic acid

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Reaction Steps

To a suspension of 50 g (0.118 mole) of (Z)-3-ethoxycarbonyl-4-(4-chlorophenyl)-4-(4-methanesulphonylphenyl)-3-butenoic acid, prepared in example 3, in 1000 ml of ethanol is added a solution of 10.4 g (0.26 mole) of sodium hydroxide in 25 ml of water. The mixture is heated under reflux for 6 hours, the precipitate is filtered off and washed with ethanol. The solid is then taken up into 500 ml of a 1N sodium hydroxide solution and the insoluble is filtered off. The aqueous phase is washed with dichloromethane and then acidified with hydrochloric acid to pH=1. After one hour's stirring, the precipitate obtained is filtered under suction, washed with water and dried to give 38.4 g of (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)-methylene]succinic acid in the form of crystals with a melting point of 199-200° C.

Provenance & Evidence