Sodium Hydroxide → HCID 23499547, compound

HRID 1836424Notes

Reaction equation

HRID 1836424 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 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-methoxy-2-(4-fluorophenyl)benzoate (9.8 g.) in methanol (75 ml.) was added 2N aqueous sodium hydroxide solution (45 ml.) and the mixture heated at reflux for 1.5 hours. The reaction was cooled to ambient temperature, filtered and the filtrate concentrated to remove the methanol. The residual aqueous phase was washed with ether, acidified to pH 1 using concentrated hydrochloric acid and extracted with ethyl acetate. The organic extracts were dried and the solvent removed to give 4-methoxy-2-(4-fluorophenyl)benzoic acid (Compound (xxix) in Scheme 3) as a white solid (7.7 g), which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customto remove the methanol
  6. washThe residual aqueous phase was washed with ether
  7. extractionextracted with ethyl acetate
  8. customThe organic extracts were dried
  9. customthe solvent removed

Sources & evidence

ORD record
ord-c1fd8b72a35a49d0b0f73706736bb79f
Source dataset
uspto-grants-2004_08
Patent number
US06777438B2

Reaction notes

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