Sulfuric Acid → 4'-Methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 4′-methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylate (150 mg, 0.46 mmol) in 1,4-dioxane (5 mL) and water (0.5 mL) was added lithium hydroxide (55 mg, 2.3 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then acidified with 2N aq. H2SO4 to pH 4-5 and concentrated in vacuo. The residue was treated with water and extracted with CH2Cl2 (10 mL×3). The combined organic layers were dried (MgSO4), and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.85 (t, J=1.6 Hz, 1H), 7.52 (d, 2H, J=8.4 Hz), 7.48 (dd, 1H=2.4, 1.2 Hz), 7.34 (dd, 1H, J=2.4, 1.6 Hz), 7.28 (d, 2H, J=8.4 Hz), 5.15 (m, 1H), 4.05-3.87 (m, 4H), 2.38 (s, 3H), 2.36-2.27 (m, 1H), 2.20-2.11 (m, 1H).

Provenance & Evidence