[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:6].O.Cl>C1COCC1>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:5]([OH:6])=[O:4])=[CH:8][CH:9]=2)=[CH:18][CH:17]=11 N NaOH (148.5 mL, 148.5 mmol) was added under nitrogen to a solution of 4′-methoxy-biphenyl-4-carboxylic acid methyl ester (12.0 g, 49.5 mmol), prepared in the previous step, in 1 L of THF plus 250 mL of water at room temperature. After the addition the reaction was refluxed for 16.5 h (overnight). After cooling to approximately room temperature the reaction was acidified by the addition of 1 N HCl and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give 4′-methoxy-biphenyl-4-carboxylic acid (11.11 g, 98%) as a white solid, mp 245-250° C.; MS (ESI) m/z 227 [M−H]−. Elemental Analysis for C14H12O3: Calc'd: C, 73.67; H, 5.30; N, 0.00; Found: C, 69.52; H, 5.01; N, 0.04.
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