Hydrochloric Acid → p-Toluenesulfinic acid

Participants

Reaction Steps

To a round bottom flask was added sodium 4-methylbenzenesulfinate (25 g, 140 mmol), MTBE (40 mL) and water (80 mL). To the reaction mixture was added concentrated HCl (12.7 mL, 154 mmol) dropwise via addition funnel over about 15 min. The resulting layers were separated and the aqueous layer extracted with MTBE (2×50 mL). The organic layers were combined and dried with MgSO4, filtered and concentrated in vacuo. The resulting solid was triturated with heptane, filtered, and dried under vacuum to provide the title compound (21.5 g, 98%). LC/MS (Table 1, Method a) Rt=1.12 min; MS m/z: 155.1 (M−H)−.

Provenance & Evidence