Hydrochloric Acid → (4-Cyclopropylsulfanylphenyl)oxoacetic acid

Participants

Reaction Conditions

Reaction Steps

In a flask (4-cyclopropylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (9.19 g, 36.71 mmol) was dissolved in toluene (20 mL) and heated to 50° C. in an oil bath. To this heated solution was then added an aqueous sodium hydroxide solution (3 M solution, 15.17 mL, 45.52 mmol) dropwise keeping the temperature of the reaction below 60° C. The reaction was then stirred at 50° C. for 1.5 h. After this time the reaction was removed from the oil bath and concentrated hydrochloric acid (3.5 mL, 42.2 mmol) was added dropwise while the reaction was still at 50° C. It was then allowed to cool to 25° C. and stirred for 16 h. The solids were filtered off and washed with water (10 mL) and toluene (10 mL) to afford (4-cyclopropylsulfanyl-phenyl)-oxo-acetic acid (3.41 g, 42%) as a white solid and used without purification.

Provenance & Evidence