Methanol → 2'-Chloro-2-(methoxymethyl)biphenyl-4-carboxylic acid

Participants

Reaction Steps

To a solution of methyl 2′-chloro-2-(methoxymethyl)biphenyl-4-carboxylate (11 g, 37.8 mmol) in a mixture of THF (50 ml), MeOH (50 ml) and water (25 ml) was added lithium hydroxide monohydrate (4.76 g, 113.5 mmol) in portions. After 12 hours at RT, the reaction mixture was concentrated and the aqueous residual layer was acidified with a concentrated aqueous solution of HCl, and then extracted with EtOAc (2×100 mL). The organic layers were washed with water and brine, combined, dried (Na2SO4) and concentrated under reduced pressure to afford of the title compound as a white solid (7.5 g, 72%). LC/MS (Method B): 275.0 (M−H)−. 1H NMR (DMSO-d6, 400 MHz) δ 13.0 (1H, brs), 8.08 (1H, s), 7.92 (1H, d), 7.58 (1H, d), 7.44 (2H, m), 7.29 (2H, m), 4.21 (1H, d), 4.13 (1H, d), 3.16 (3H, s).

Provenance & Evidence