Acetic Acid → Benzaldehyde

HRID 1182338Notes

Reaction equation

HRID 1182338 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:8]N1C(=O)N(O)C(=O)N(O)C1=O.[C:20]([OH:23])(=[O:22])[CH3:21].O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[C:20]([OH:23])(=[O:22])[C:21]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1.[CH:7](=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 1140TolueneHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 240BenzaldehydeHCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.276 g of toluene, 0.005 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1% by mole relative to toluene), 5 g of acetic acid and 0.004 g of cobalt (II) acetate.4 H2O was stirred at 60° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 6 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield benzoic acid and benzaldehyde in 49% and 3% yields, respectively, at 53% conversion of toluene.

Sources & evidence

ORD record
ord-7841472685e04e7b9ba8e4b73eb69f8d
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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