Acetic Acid → 4-Nitrobenzoic Acid

HRID 436020Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8]C(C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[K+].[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

Reactant 3

HCID 176Acetic Acid

HCID 74734-Nitrotoluene

HCID 253877Potassium Bromide

Product 1

HCID 61084-Nitrobenzoic AcidYield 86.5%

Procedure

The oxidation of 300 g of p-nitrotoluene in 2500 ml of glacial acetic acid, in the presence of 4 g KBr and 15 g Co(OA)2 . 4H2O, at a reaction temperature of 185° C and a reaction time of 3 hours, gave a yield of 86.5% of p-nitrobenzoic acid. The absorption of oxygen began at 165° C. During the reaction CO2 was detected qualitatively in the residual gas. After the addition of 500 ml of benzene, 103 g of water (240% of the theory) was distilled azeotropically from the mother liquor.

Sources & evidence

ORD record: ord-38517bc80f0b4f6b8c4ea94818b11f08
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04007223

Reaction notes

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