Methanol → 4'-(tert-Butyl)-[1,1'-biphenyl]-2-carboxylic acid

Participants

Reaction Steps

Crude 4′-tert-butylbiphenyl-2-carboxylic acid ethyl ester (33 g, ˜117 mmol) was taken up in a mixture of THF (100 mL), methanol (50 mL) and water (40 mL). Lithium hydroxide monohydrate (7.36 g, 176 mmol) was added and the reaction mixture was allowed to stir at room temperature for 3 days. The mixture was extracted three times with diethyl ether. The aqueous phase was then acidified using aq. 6N HCl and extracted three times with EtOAc. The combined EtOAc layers were dried over MgSO4, filtered and concentrated. The solid residue was triturated with hexane to afford the title compound as a white solid (18.7 g, 63%). 1H NMR (selected signals, DMSO-d6): 7.66 (dd, 1H), 7.53 (m, 1H), 7.41 (d, 2H), 7.25 (d, 2H), 1.29 (s, 9H).

Provenance & Evidence