Sodium Hydroxide → 6-Phenylsulfanyl-hexa-2,4-dienoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-phenylsulfanyl-hexa-2,4-dienoic acid methyl ester (0.34 g, 1.45 mmol) in methanol (5 mL) were added aqueous sodium hydroxide (1M, 5 mL, 5 mmol) and distilled water (20 mL). The stirred mixture was heated at reflux for 1 hour, allowed to cool to 20° C., and then concentrated under reduced pressure to about 10 mL. The aqueous solution was washed with diethyl ether (50 mL) and then poured onto a mixture of ethyl acetate (50 mL) and hydrochloric acid (2M, 10 mL) at 0° C. The mixture was shaken, the organic layer was separated and washed successively with saturated aqueous sodium hydrogen carbonate (25 mL), distilled water (25 mL), and brine (25 mL), then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a pale yellow solid that was recrystallised from diethyl ether/hexanes to give the title compound (0.30 g, 93%) as a white solid, mp 108-110° C.

Provenance & Evidence