Dimethyl Sulfide → 4-Hydroxyphenyl methanesulfonate

Participants

Reaction Steps

4-(Benzyloxy)phenyl methanesulfonate (5.31 g, 19.08 mmol) was dissolved in dry DCM (70 mL) under nitrogen atmosphere. Boron trifluoride diethyl etherate (10.83 g, 76.31 mmol) was added followed by dimethyl sulfide (4.74 g, 76.31 mmol) and the reaction mixture was stirred at rt for 3 h. The reaction mixture was poured onto ice and the aqueous layer was extracted with DCM. The organic layers were combined, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.96 g, 82.5%). 1H NMR (500 MHz, CDCl3): δ 3.14 (s, 3H), 5.51 (s, 1H), 6.83 (d, 2H), 7.14 (d, 2H); 13C NMR (125 MHz, CDCl3): δ 37.35, 116.74, 123.49, 142.68, 155.06.

Provenance & Evidence