Sodium Hydroxide → 2-Methyl-[1,1'-biphenyl]-4-carboxylic acid

HRID 1174969Notes

Reaction equation

HRID 1174969 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([CH3:17])[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O>[CH3:17][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53670602Methyl 2-methyl-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 215218102-Methyl-[1,1'-biphenyl]-4-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-methyl-biphenyl-4-carboxylic acid methyl ester (0.10 g, 0.44 mmol) in CH3OH (5 mL) and H2O (0.5 mL) is reacted with NaOH (88 mg, 2.2 mmol) at reflux for 2 h. Organic solvent is removed in vacuo, the residue is diluted with H2O, and extracted with Et2O. The aqueous layer is acidified with 5 M HCl, extracted with Et2O, dried with MgSO4, filtered and concentrated to give the title compound as a white solid (72 mg, 77%).

Workup

  1. temperatureat reflux for 2 h
  2. customOrganic solvent is removed in vacuo
  3. additionthe residue is diluted with H2O
  4. extractionextracted with Et2O
  5. extractionextracted with Et2O
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0cfd458d21ff454f8be8868a9f34c742
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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