Lithium Hydroxide → 2'-Cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 2′-cyano-5-(1,2-dihydroxyethyl)-4′-methylbiphenyl-3-carboxylate (140 mg, 0.45 mmol) in 1,4-dioxane (5 mL) and water (2 mL) was added lithium hydroxide (40 mg, 1.67 mmol). The reaction mixture was stirred at rt for 6 h, and then treated with aq. NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried over anhydrous MgSO4, and concentrated to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.21 (m, 1H), 8.13 (m, 1H), 7.87 (m, 1H), 7.73 (s, 1H), 7.66-7.61 (m, 1H), 7.58 (d, 1H, J=7.6 Hz), 4.91 (dd, 1H, J=7.2, 4.4 Hz), 3.75 (dd, 1H, J=11.2, 4.4 Hz), 3.65 (dd, 1H, J=11.2, 7.2 Hz), 2.47 (s, 3H).

Provenance & Evidence