Hydrochloric Acid → 2'-Cyano-5-(2,3-dihydroxypropoxy)-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 2′-cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4′-methylbiphenyl-3-carboxylic acid (63 mg, 0.17 mmol) in THF (3 mL) was added 1 M of aq. HCl solution (3 mL, 3 mmol). The reaction mixture was stirred at room temperature for 4 hours, and then concentrated in vacuo. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.77 (t, 1H, J=1.6 Hz), 7.67 (m, 2H), 7.58 (dd, 1H, J=8.0, 2.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.38 (t, 1H, J=2.0 Hz), 4.19 (dd, 1H, J=9.6, 4.0 Hz), 4.10 (dd, 1H, J=9.6, 6.0 Hz), 4.02 (m, 1H), 3.72 (dd, 1H, J=11.2, 5.6 Hz), 3.67 (dd, 1H, J=11.2, 5.6 Hz), 2.45 (s, 3H).

Provenance & Evidence