Acetic Acid → 4-Nitrobenzoic Acid

HRID 436023

Reaction equation

HRID 436023 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8]C(C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH4+].[Br-].[C:13]([OH:16])(=[O:15])[CH3:14]>>[N+:1]([C:4]1[CH:9]=[CH:8][C:14]([C:13]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 74734-NitrotolueneHCID 25514Ammonium Bromide

Product 1

HCID 61084-Nitrobenzoic Acid

Procedure

750 g of p-nitrotoluene was oxidized in 2250 ml of glacial acetic acid, after the addition of 15 g of NH4Br, 4.5 g of Co(OAc)2 . 4H2O and 4.5 g of Mn(OAc)2 . 4H2O, at a reaction temperature of 175° C. The reaction product was washed and dried as before. 795 g (87% of the theory) of brown-discolored p-nitrobenzoic acid was obtained, having a melting point of 235°-36° C. The solution of 1 g of the product in 10 g of dimethylsulfoxide has a value of 40 on the iodine color scale. After recrystallization three times from glacial acetic acid, the melting point was 237°-40° C, while the iodine number remained unchanged.

Workup

  1. customat a reaction temperature of 175° C
  2. washThe reaction product was washed
  3. customdried as before

Sources & evidence

ORD record
ord-d6fb7cb9aaa545c588b13cf3922d0302
Source dataset
uspto-grants-1977_02
Patent number
US04007223

Linked notes

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