Acetic Acid → 2-Nitrotoluene

HRID 9752

Reaction equation

HRID 9752 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].ON1C(=O)N(O)C(=O)N(O)C1=O.[C:23]([OH:26])(=[O:25])[CH3:24]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:24]=1[C:23]([OH:26])=[O:25])([O-:3])=[O:2].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 69442-NitrotolueneHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 69442-NitrotolueneHCID 110872-Nitrobenzoic acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

In an autoclave, 0.274 g of 2-nitrotoluene, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to 2-nitrotoluene), 5 g of acetic acid, 0.003 g of cobalt (II) acetate.4H2O, 0.001 g of manganese(II) acetate.4H2O and 0.018 g of NO2 were placed. The autoclave was charged with 1 MPa of air and placed in a heated oil bath. The mixture was stirred at 150° C. for 14 hours. After the completion of reaction, the autoclave was placed on cold water to cool down the reaction mixture quickly. The resulting mixture was analyzed by gas chromatography and was found to yield 2-nitrobenzoic acid in 62% yield at 67% conversion of 2-nitrotoluene.

Workup

  1. additionThe autoclave was charged with 1 MPa of air
  2. customplaced in a heated oil bath
  3. customAfter the completion of reaction
  4. temperatureto cool down the reaction mixture quickly

Sources & evidence

ORD record
ord-98cca51794be4ca59ebc9de69d50807e
Source dataset
uspto-grants-2006_08
Patent number
US07091342B2

Linked notes

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