Acetic Acid → 4-Nitrobenzoic Acid

HRID 436019Notes

Reaction equation

HRID 436019 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-NitrotolueneHCID 253877Potassium Bromide

Product 1

HCID 61084-Nitrobenzoic AcidYield 99%

Procedure

With the addition of 8 g KBr and 50 g Co(OAc)2 . 4H2O, 600 grams of p-nitrotoluene was oxidized in 2500 ml of glacial acetic acid at a reaction temperature of 120° C. The absorption of oxygen began at 95° C and ended 3 hours later. While the minimum oxygen content in the residual gas was determined to be 3.6%, qualitative testing for CO2 remained negative. 681 g of p-nitrobenzoic acid (93% of the theory) was isolated from the reaction mixture, with a neutralization equivalent of 167.5 and a melting point of 239° C. An additional 45 g of p-nitrobenzoic acid was found acidimetrically in the residue obtained by concentrating the mother liquor (total yield 99% of the theory).

Workup

  1. customThe absorption of oxygen
  2. custombegan at 95° C

Sources & evidence

ORD record
ord-33fcb049bf7b4e73800e1cc2661734ed
Source dataset
uspto-grants-1977_02
Patent number
US04007223

Reaction notes

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