2-Chlorobenzenesulfonyl chloride → 3-(2-Chlorophenylsulfonyloxy)-5-methylphenol

Participants

Reaction Steps

Orcinol monohydrate (1.42 g, 10 mmol) and 2-chlorobenzenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether(30 mL). The biphasic mixture was stirred vigorously at room temperature for 2 days. The reaction mixture was quenched with 50 mL of water and extracted into ethyl acetate. (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (20% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.15 g, 71%).

Provenance & Evidence