Sodium Hydroxide → 2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate (15 g, 62.2 mmol) in THF (100 mL) was added a 10% aqueous solution of sodium hydroxide (100 mL) and the mixture was heated at 100° C. overnight. THF was removed under reduced pressure and the aqueous residue was washed with EtOAc. The aqueous layer was then acidified with a 3N aqueous solution of HCl (until pH 2-3) and extracted with DCM. The organic phase was washed with water and dried over sodium sulfate and concentrated under reduced pressure to obtain get the title compound as a white solid (13.5 g, 95%). 1H NMR (DMSO-d6, 400 MHz) δ 12.89 (bs, 1H), 7.89 (s, 1H), 7.81 (m, 1H), 7.32-7.23 (m, 3H), 7.19-7.11 (m, 1H), 7.06 (m, 1H), 2.04 (s, 3H), 1.98 (s, 3H). LC/MS (Method B): 227.0 (M+H)+. HPLC (Method B), Rt 4.1 min (purity: 99.6%).

Provenance & Evidence