Sodium Hydroxide → HCID 23499547, compound

HRID 1251882Notes

Reaction equation

HRID 1251882 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23499548Methyl 4-methoxy-2-(4-fluorophenyl)benzoate

Product 1

HCID 23499547HCID 23499547, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-methoxy-2-(4-fluorophenyl)benzoate (9.8 g; 0.029 mol) in methanol (75 ml) was added 2N aqueous sodium hydroxide solution (45 ml) and the mixture heated at reflux for 1.5 h. The reaction was cooled to ambient temperature, filtered and the filtrate concentrated in vacuo to remove the methanol. The residual aqueous phase was washed with diethyl ether, acidified to pH 1 with concentrated HCl and extracted with ethyl acetate. The organic extracts were dried (MgSO4) and the solvent removed in vacuo to give 4-methoxy-2-(4-fluorophenyl)benzoic acid as a white solid (7.7 g), which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 h
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto remove the methanol
  6. washThe residual aqueous phase was washed with diethyl ether
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic extracts were dried (MgSO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-04662595b38149218818428512bf04e4
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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