Acetic Acid → 4-Nitrobenzaldehyde

HRID 1182340Notes

Reaction equation

HRID 1182340 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:11]N1C(=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:9]=[CH:8][C:24]([C:23]([OH:26])=[O:25])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 74734-NitrotolueneHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 5414-NitrobenzaldehydeHCID 61084-Nitrobenzoic Acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

In an autoclave, 0.274 g of 4-nitrotoluene, 0.011 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to 4-nitrotoluene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4 H2O and 0.001 g of manganese(II) acetate .4 H2O were placed. The autoclave was charged with 1 MPa of air and placed in a heated oil bath. The mixture was stirred at 130° 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 4-nitrobenzoic acid and 4-nitrobenzaldehyde in 85% and 1% yields, respectively, at 91% conversion of 4-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-1730014830c441c7abfa583295b9060a
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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