Sulfuric Acid → 5-(4-Hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4′-methylbiphenyl-3-carboxylate (140 mg, 0.40 mmol) in 1,4-dioxane (2.8 mL) and water (2.8 mL) was added lithium hydroxide (50 mg, 2.1 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then acidifized with 2N aq. H2SO4 to pH 4-5 and concentrated in vacuo. The residue was treated with water and extracted with EtOAc (10 mL×2). The combined organic layers were dried (MgSO4) and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.87 (t, J=1.6 Hz, 1H), 7.55-7.51 (m, 3H), 7.42 (t, J=2.0 Hz, 1H), 7.28 (d, J=7.6 Hz, 2H), 4.84 (d, J=4.4 Hz, 1H), 4.38 (d, J=4.0 Hz, 1H), 4.23 (dd, J=10.4, 4.4 Hz, 1H), 4.05 (dd, J=9.6, 4.4 Hz, 1H), 3.94 (dd, J=10.4, 1.6 Hz, 1H), 3.77 (dd, J=9.6, 1.6 Hz, 1H), 2.38 (s, 3H).

Provenance & Evidence