Hydrogen Peroxide → 2,4,5-Trichlorobenzoic acid

HRID 374617Notes

Reaction equation

HRID 374617 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[C:14]([Cl:18])=[CH:13][C:3]=1[C:4](C1C=CC=CC=1F)=[O:5].OO.FC1C=CC=CC=1[OH:28]>ClCCl.[N+](C1C=CC=CC=1C(=[Se])O)([O-])=O>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[C:14]([Cl:18])=[CH:13][C:3]=1[C:4]([OH:5])=[O:28]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 97072-FluorophenolHCID 18997588HCID 18997588, compound

Product 1

HCID 57862,4,5-Trichlorobenzoic acidYield 152.2%

Reagents, catalysts & solvents 2

HCID 178526589HCID 178526589, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

7.6 g (25mmol) of 2,4,5-trichloro-2'-fluorobenzophenone, 4.3 g (0.115 mol) of 90% hydrogen peroxide and 0.25 g of 2-nitrobenzoselenic acid were stirred for 24 h in 50 ml of dichloromethane. The insoluble constituents were then filtered off, water was added and the organic phase was separated off. After removal of the solvent, the residue was heated with 120 g of 60% sulfuric acid for 8 h to hydrolyze the ester present. 1.55 g (13.8 mmol, 55%) of 2-fluorophenol could then be separated off by steam distillation. 4.8 g (21 mmol, 85%) of 2,4,5-trichlorobenzoic acid (crude (GC) ca. 95%) were isolated from the mother liquor.

Workup

  1. filtrationThe insoluble constituents were then filtered off
  2. additionwater was added
  3. customthe organic phase was separated off
  4. customAfter removal of the solvent
  5. temperaturethe residue was heated with 120 g of 60% sulfuric acid for 8 h

Sources & evidence

ORD record
ord-be0d0b6ff3af42b787d5fd6d3d400b86
Source dataset
uspto-grants-1996_01
Patent number
US05481032

Reaction notes

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