Acetic Acid → 4-Nitrobenzoic Acid

HRID 436022Notes

Reaction equation

HRID 436022 reaction equation
[K+].[Br-].[N+:3]([C:6]1[CH:11]=[CH:10]C(C)=[CH:8][CH:7]=1)([O-:5])=[O:4].[C:13]([OH:16])(=[O:15])[CH3:14]>>[N+:3]([C:6]1[CH:11]=[CH:10][C:14]([C:13]([OH:16])=[O:15])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 74734-Nitrotoluene2×HCID 253877Potassium Bromide

Product 1

HCID 61084-Nitrobenzoic Acid

Procedure

In the presence of 40 g of Co(OAc)2 . 4H2O and 8 g of KBr, 600 grams of p-nitrotoluene was oxidized in 2500 ml of glacial acetic acid. The product was processed as in the above Example 15; after the addition of 600 more grams of p-nitrotoluene, the oxidation was performed again, and the procedure was repeated one more time. The reaction temperature in all three procedures was not increased above 130° C. Filtration of the 3 reaction solutions yielded 2096 grams of p-nitrobenzoic acid (95.5% of the theory). After the addition to the mother liquors of 400 ml of 1,2-dichloroethane for each batch, 247 grams of water (99.5% of the theory) were removed by azeotropic distillation.

Workup

  1. temperatureThe reaction temperature in all three procedures was not increased above 130° C
  2. filtrationFiltration of the 3 reaction solutions

Sources & evidence

ORD record
ord-1909db0eb0c54aab86462888ba5899a3
Source dataset
uspto-grants-1977_02
Patent number
US04007223

Reaction notes

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