Acetic Acid → 2,3-difluoro-4-hydroxybenzoic acid

HRID 1166716Notes

Reaction equation

HRID 1166716 reaction equation
[F:1][C:2]1[C:7]([F:8])=C(C#N)[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([OH:15])(=[O:14])[CH3:13]>O.OS(O)(=O)=O>[F:8][C:7]1[C:2]([F:1])=[C:3]([OH:11])[CH:4]=[CH:5][C:13]=1[C:12]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27369782,3-Difluoro-4-hydroxybenzonitrile

Product 1

HCID 27793072,3-difluoro-4-hydroxybenzoic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 2,3-difluoro-4-cyanophenol (1 g, 6.45 mmol) in water (8 mL), H2SO4 (8 mL), and acetic acid (8 mL) was refluxed for 48 hours. The solvents were removed by rotary evaporation to give a slurry which was poured onto ice. The product precipitated out of solution and filtered. The solid was washed with water and dried to give 2,3-difluoro-4-hydroxybenzoic acid (800 mg, 71%).

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThe solvents were removed by rotary evaporation
  3. customto give a slurry which
  4. additionwas poured onto ice
  5. customThe product precipitated out of solution
  6. filtrationfiltered
  7. washThe solid was washed with water
  8. customdried

Sources & evidence

ORD record
ord-6073920baf8d42518caede8960c366b4
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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