Hydrochloric Acid → Methanesulfonic acid 4-hydroxymethyl-phenyl ester

Participants

Reaction Steps

4-Methanesulfonyloxy-benzoic acid methyl ester (330 mg, 1.43 mmol) was dissolved in anhyrous THF (10 mL) and LiAlH4 (109 mg, 2.86 mmol) was added. The resulting suspension was stirred at room temperature until no starting material was left. Excess LiAlH4 was hydrolyzed with aq. HCl (2N) and the remaining suspension was extracted with EtOAc. The organic layer was seperated, dried (MgSO4) and evaporated and the remaining crude product was purified by flash chromatography using n-heptane/EtOAc 3:7 as the eluent to afford the title compound as an oil (202 mg, 93%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.40 (d, 2H), 7.23-7.25 (d, 2H), 4.67 (s br, 2H), 3.10 (s, 3H).

Provenance & Evidence