Water → HCID 17871262, compound

Participants

Reaction Steps

To a stirred solution of 2-methylsulfonylbenzenesulphonyl chloride (3.63 g, 14.2 mmol) and orcinol monohydrate (2.02 g, 14.2 mmol) in dichloromethane (50 mL) was added saturated NaHCO3 aqueous solution (30 mL) dropwise in 30 min. After stirred vigorously at room temperature for 3 days, water was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered, and concentrated to half of the volume (˜60 mL). Hexanes (30-40 mL) were added to initiate crystallization. After standing overnight, the mixture was filtered, and the solid was rinsed with small amount of diethyl ether and dichloromethane to give the title compound as a pale pink solid (2.18 g, 44.8%). 1H NMR (CDCl3) δ 8.43 (dd, 1H, J=1.3, 7.9 Hz), 8.11 (dd, 1H, J=1.3, 7.9 Hz), 7.87 (td, 1H, J=1.4, 7.7 Hz), 7.73 (td, 1H, J=1.4, 7.7 Hz), 6.58 (s, 1H), 6.55 (s, 1H), 6.51 (s, 1H), 3.45 (s, 3H), 2.21 (s, 3H).

Provenance & Evidence