[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[OH:10]N1C(=O)N(O)C(=O)N(O)[C:12]1=[O:21].[O:22]=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:12]([OH:21])=[O:22])=[CH:2][CH:3]=1)#[N:8].[C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH:9]=[O:10])=[CH:2][CH:3]=1)#[N:8]A mixture of 0.351 g of p-tolunitrile, 0.005 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1% by mole relative to p-tolunitrile), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 14 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield 4-cyanobenzoic acid and 4-cyanobenzaldehyde in 74% and 1% yields, respectively, at 81% conversion of p-tolunitrile.
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