Phenol → 4-Hydroxybenzene-1-sulfonyl chloride

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Reaction Steps

To chlorosulfonic acid (248 mL, 3.37 mol) cooled to −3° C. was added dropwise a solution of phenol (70 g, 0.744 mot) in 250 mL of anhydrous methylene chloride over a period of 1 hour under argon gas. The mixture was warmed to rt over 1 h and was stirred at rt for 1.5 h. The mixture was poured over ice, stirred for 30 min, and was extracted with methylene chloride (4×2 L). The resulting organic layer was dried over MgSO4 and concentrated in vacuo to yield 4-hydroxybenzenesulfonyl chloride as a sticky brown solid (41.49 g, 29%): 1H NMR (400 MHz, d6-DMSO) δ 7.29–7.38 (d, 2 H), 6.58–6.69 (d, 2 H).

Provenance & Evidence