HCID 22118408, compound → HCID 15477826, compound

Participants

Reaction Conditions

Reaction Steps

17.8 Grams (about 15 mmol) of a 6.4 wt % sodium hypochlorite aqueous solution was placed in a 100-ml three-necked round-bottomed flask, and cooled to 15~20° C., and then a solution of 1.26 g (4.26 mmol) of 6-acetyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide in 8 ml of dioxane was gradually added. The mixture was stirred at 15~20° C. with external cooling for 30 minutes, and then stirred at room temperature (temperature-increased to about 30° C.) for 3 hours. The reaction mixture was diluted with about 50 ml of water and washed with chloroform twice. A sodium sulfate aqueous solution was added to an aqueous layer to decompose excess hypochlorite, and then the aqueous solution was neutralized and acidified with a 5 wt % hydrochloric acid aqueous solution to give a white solid. The solid was extracted with ethyl acetate, and an organic layer was washed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 1.06 g (yield 84%) of 6-carboxy-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide in the form of a white solid.

Provenance & Evidence