Phenol → Phenyl methanesulfonate

To a solution of 40.0 g (0.42 mol, 1 eq.) of phenol in 250 mL of dichloromethane at 0° C. was added 250 mL (1.8 mol, 4.2 eq.) of triethylamine. After 5 min, 49.3 mL (0.64 mol, 1.5 eq.) of methanesulfonyl chloride was added dropwise over 20 min. The resulting cloudy yellow solution was warmed to RT and stirred for 14 h. The reaction was partitioned between ether (250 mL) and water (100 mL) and the resulting organic layer was washed with cold 6N hydrochloric acid (2×200 mL). The combined aqueous layers were extracted with ether (2×50 mL) and the combined organic layers were washed with water (100 mL), saturated sodium bicarbonate (200 mL), brine (200 mL), dried (MgSO4) and concentrated. Recrystallization of the orange solid from isopropanol afforded 44.94 g (61%) of the title compound as light yellow crystals, mp 58.0°-58.5° C.

1. customThe reaction was partitioned between ether (250 mL) and water (100 mL)
2. washthe resulting organic layer was washed with cold 6N hydrochloric acid (2×200 mL)
3. extractionThe combined aqueous layers were extracted with ether (2×50 mL)
4. washthe combined organic layers were washed with water (100 mL), saturated sodium bicarbonate (200 mL), brine (200 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customRecrystallization of the orange solid from isopropanol

ORD record

ord-16c5f4dd14464cc4ad2174774e73620c

Source dataset

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05470845