3-(2-Oxopropyl)benzoic acid → 3-(2-Hydroxy-2-methylpropyl)benzoic acid

Participants

Reaction Steps

CH3MgBr (3.0 M in THF, 11.2 mL, 33.7 mmol) was added slowly to a stirring solution of 3-(2-oxopropyl)benzoic acid (2 g, 11.2 mmol) in THF (100 mL) at 0° C. The resulting suspension was allowed to warm to rt then stirred overnight. The reaction mixture was diluted with H2O (50 mL) then quenched with 5 N HCl (pH<3). The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 (s), and concentrated to give a yellow oil. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (1.36 g, 62%) as a white solid. ES/MS calcd. for C11H14NaO3+ 217.1. found m/z=217.2 (M+Na)+.

Provenance & Evidence