Lithium Hydroxide → 3-Hydroxy-4-(2-methylphenyl)benzoic acid
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[OH-].[Li+]>C1COCC1.O>[OH:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 2-hydroxy-2′-methyl-1,1′-biphenyl-4-carboxylate (12 g, 0.05 mol) in a mixture of THF/water (150 mL:15 mL) was added lithium hydroxide (6.23 g, 0.1485 mol) in portions. After being stirred at RT for 24 h, the reaction mass was evaporated to dryness and the residue diluted with little amount of water. The aqueous phase was acidified with conc.hydrochloric acid and extracted with EtOAc. Organic layer was washed with brine solution and was dried over Na2SO4. Evaporation of the solvents afforded the title compound as a white solid (10 g, 89%). 1H NMR (DMSO-d6, 400 MHz) δ 12.72 (1H, bs), 9.78 (1H, bs), 7.50 (1H, s), 7.41-7.43 (1H, m), 7.08-7.24 (5H, m), 2.09 (3H, s). LC/MS (Method A): 227 (M−H)−. HPLC (Method B), Rt 4.09 min (purity: 99.69%).