Hydrogen Peroxide → 2,4-Dichloro-5-fluorobenzoic acid

HRID 374609

Reaction equation

HRID 374609 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[C:14]([F:18])=[CH:13][C:3]=1[C:4](C1C=CC(F)=CC=1)=[O:5].[OH:19]O>OS(O)(=O)=O.O=S(=O)=O>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[C:14]([F:18])=[CH:13][C:3]=1[C:4]([OH:5])=[O:19]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 18997590HCID 18997590, compound

Product 1

HCID 6881382,4-Dichloro-5-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Conditions

Temperature
50 °C

Procedure

28.7 g (0.1 mol) of 2,4-dichloro-4',5-difluorobenzophenone are dissolved in 250 g of 10% oleum, and 25 g of 50% hydrogen peroxide solution are added at temperatures up to 30° C. When the metered addition has ended (30 min), the mixture is heated for 8 h at 50° C. and, after cooling, is poured on to 250 g of ice. This mixture is kept for 8 h at 140° C. and 4-fluorophenol is then recovered by steam distillation (7.5 g, 0.0673 mol, 67%, m.p. (DSC) 42.6° C.). 2,4-dichloro-5-fluorobenzoic acid is isolated as described in Example 1 (17.0 g, 0.0813 mol, 81%, m.p. 143°-145° C.). (DSC =differential scanning calorimetry)

Workup

  1. additionWhen the metered addition
  2. custom(30 min)
  3. temperatureafter cooling
  4. distillation4-fluorophenol is then recovered by steam distillation (7.5 g, 0.0673 mol, 67%, m.p. (DSC) 42.6° C.)

Sources & evidence

ORD record
ord-92edf459b2944c84a9abcea8d2cc2943
Source dataset
uspto-grants-1996_01
Patent number
US05481032

Linked notes

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