Acetic Acid → Thioxanthene, 10,10-dioxide

Participants

Reaction Conditions

Reaction Steps

Thioxanthene, 29 (2.9 g, 14.6 mmol) was dissolved in glacial acetic acid (90 mL). While under argon, the solution was treated with hydrogen peroxide (6.12 mL, 62.9 mmol of a 35% by wt water solution) and the reaction stirred at 100° C. for 1.5 hr. The reaction was cooled to room temperature, poured into water (250 mL), stirred 0.5 hrs and filtered to give a white solid. The solid was dissolved in CH2Cl2, washed with 5% sodium bisulfite (aq), dried over Na2SO4, filtered and concentrated to dryness in vacuo. Treatment of the resulting oil with methanol gave the title compound as a white solid.

Provenance & Evidence