Lithium Hydroxide → 3-Hydroxy-4-(2-methylphenyl)benzoic acid

HRID 219838Notes

Reaction equation

HRID 219838 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

HCID 3939Lithium HydroxideHCID 58554208Methyl 2-hydroxy-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 532248533-Hydroxy-4-(2-methylphenyl)benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

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%).

Workup

  1. customthe reaction mass was evaporated to dryness
  2. additionthe residue diluted with little amount of water
  3. extractionhydrochloric acid and extracted with EtOAc
  4. washOrganic layer was washed with brine solution
  5. dry with materialwas dried over Na2SO4
  6. customEvaporation of the solvents

Sources & evidence

ORD record
ord-b4481687a1a442089f0c42626cc03b2b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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