Acetic Acid → 2,3-Dichlorobenzoic acid

HRID 2259465Notes

Reaction equation

HRID 2259465 reaction equation
[Br-].[Na+].[Cl:3][C:4]1[C:5]([Cl:11])=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1.OO.[C:14]([OH:17])(=[O:16])[CH3:15]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[Cl:3][C:4]1[C:5]([Cl:11])=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]=[O:16].[Cl:3][C:4]1[C:5]([Cl:11])=[C:15]([CH:7]=[CH:8][CH:9]=1)[C:14]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 34702Benzene, 1,2-dichloro-3-methyl-2×HCID 253881Sodium Bromide

Product 2

HCID 57652,3-Dichlorobenzoic acidYield 23.8%HCID 357452,3-DichlorobenzaldehydeYield 15.2%

Reagents, catalysts & solvents 1

HCID 61372Cobalt(II) acetate tetrahydrateCatalyst

Procedure

The procedure of Example I was repeated, but this time cobalt (II) acetate tetrahydrate (0.012 moles), sodium bromide (0.05 moles), dichlorotoluene (0.074 moles), acetic acid (100 g) and hydrogen peroxide (70%, 0.68 moles) were used and the reaction was performed at 90° C. for three hours. The final reaction mixture, analysed by HPLC, revealed that 66.0% of the dichlorotoluene had been consumed, yielding products including dichlorobenzaldehyde (15.2% yield) and dichlorobenzoic acid (23.8% yield).

Workup

  1. customThe final reaction mixture
  2. customhad been consumed
  3. customyielding products

Sources & evidence

ORD record
ord-2f3c76ec3bdf4706a3d7f16e909691e8
Source dataset
uspto-grants-1995_12
Patent number
US05473101

Reaction notes

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