Sodium Hydroxide → 6-Carboxy-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide

Participants

Reaction Conditions

Reaction Steps

28 Grams (77 mmol) of 8-chloro-6-ethoxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide was dissolved in 100 ml of ethanol, and 13.6 g (208 mmol) of a zinc powder was added. Further, a solution of 27 g (400 mmol) of sodium hydroxide in 50 ml of water and 50 ml of ethanol was added, and then the mixture was stirred under heat at 60° C. for 6 hours. After the completion of the reaction, an insoluble solid was removed by filtration, and an aqueous layer was washed with methylene chloride. The aqueous layer was acidified with a 5 wt % hydrochloric acid aqueous solution and extracted with ethyl acetate, and an organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 16.2 g (yield 69%) of the titled compound.

Provenance & Evidence