[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]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.4H2O and 0.001 g of manganese(II) acetate.4H2O 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.
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