Acetic Acid → 2-Chlorobenzoic Acid

HRID 746302Notes

Reaction equation

HRID 746302 reaction equation
[Cl:1][C:2]1C=[CH:6][CH:5]=[CH:4][C:3]=1C.[C:9]([OH:12])(=[O:11])[CH3:10]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:10]=1[C:9]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 72382-Chlorotoluene

Product 1

HCID 83742-Chlorobenzoic AcidYield 85.8%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 253881Sodium BromideCatalyst

Conditions

Temperature
25 °C

Procedure

Analogously to Example 1, 300 g of o-chlorotoluene was oxidized in the presence of 100 g of acetic acid, 3 g of cobalt acetate tetrahydrate and 1.5 g of sodium bromide at a pressure of 25 bar, a temperature of 110°-130° C., and a gas exhaust rate of 3 1/min. After the oxidation had ended, 450 g of 50% acetic acid was added, the mixture was cooled to 25° C. and filtered, and the filter cake was washed with 750 g of 50% acetic acid, the mother liquor (314.5 g) and washing filtrates (693.5 g) being recovered separately. The dried filter cake yielded 318.5 g of o-chlorobenzoic acid.

Workup

  1. customa temperature of 110°-130° C.
  2. filtrationfiltered
  3. washthe filter cake was washed with 750 g of 50% acetic acid
  4. washthe mother liquor (314.5 g) and washing filtrates (693.5 g)
  5. custombeing recovered separately
  6. filtrationThe dried filter cake

Sources & evidence

ORD record
ord-88d12c21a8bd4069be1f5b712d78708b
Source dataset
uspto-grants-1986_07
Patent number
US04603220

Reaction notes

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