To a magnetically stirred solution of trans-stilbene (0.724 g, 4.02 mmol) in 5 mL of acetone in a 125-mL stoppered Erlenmeyer flflask was added a solution of DMDO in acetone (0.062 M, 66 mL, 4.09 mmol) at room temperature (about 20 °C). The progress of the reaction was followed by GLC analysis, which indicated that transstilbene was converted into the oxide in 6 h. Removal of the excess acetone on a rotary evaporator (20 °C, 15 mm Hg) afforded a white crystalline solid. The solid was dissolved in CH2Cl2 (30 mL) and dried over anhydrous Na2SO4. The drying agent was removed by fifiltration and washed with CH2Cl2. The solution was concentrated on a rotary evaporator, and the remaining solvent was removed (20 °C, 15 mmHg) to give an analytically pure sample of the oxide (0.788 g, 100%).
Reference: Murray, R. W.; Singh M. Org. Syn. 1998, Collective Volume 9, 288−293.
