Sulfuric Acid → 4'-Methyl-5-((tetrahydrofuran-2-yl)methoxy)biphenyl-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 4′-methyl-5-((tetrahydrofuran-2-yl)methoxy)biphenyl-3-carboxylate (130 mg, 0.40 mmol) in 1,4-dioxane (5 mL) and water (0.5 mL) was added lithium hydroxide (50 mg, 2.1 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): 7.84 (t, J=1.6 Hz, 1H), 7.54-7.50 (m, 3H), 7.38 (dd, 1H, J=2.8, 1.6 Hz), 7.27 (d, 2H, J=8.0 Hz), 4.34-4.27 (m, 1H), 4.12 (dd, 1H, J=10.0, 3.6 Hz), 4.04 (dd, 1H, J=10.0, 6.4 Hz), 3.97-3.80 (m, 2H), 2.38 (s, 3H), 2.20-1.80 (m, 4H).

Provenance & Evidence