Methanol → 2-(4-Methylphenyl)benzoic acid

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Reaction Steps

Methyl 4-methylbiphenyl-2-carboxylate (10.0 g, 44.2 mmol, 1 eq), 0.5 N KOH in methanol (265.5 ml, 133 mmol, 3 eq), and water (50 mL) were mixed and refluxed under N2. After 5 hours, the solvent was removed in ml and water (200 mL) and ethyl acetate (200 mL) added. The aqueous layer was acidified with concentrated hydrochloric acid to a pH of 3 and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×200 mL), the organic layers collected, dried (MgSO4) and the solvent removed in y3=to yield 8.71 g of a white solid; m.p. 140.0°-145.0° NMR (206 MHz, DMSO-d6 δ 7.72 (d, 1H, J=7 Hz); 7.56 (t, 1H, J=7 Hz); 7.45 (d, 1H, J=7 Hz); 7.40 (t, 1H, J=7 Hz); 7.25 (9, 411); 2.36 (s, 3H). Anal. Calcd. for C14H12O2; C, 79.23; H, 5.70. Found: C, 79.22; H, 5.47.

Provenance & Evidence