Oxygen → Cresatin

HRID 1182334Notes

Reaction equation

HRID 1182334 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].ON1C(=O)N(O)C(=O)N(O)[C:14]1=[O:23].N(C(C)(C)C#N)=NC(C)(C)C#N.[O:36]=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.C(O)(=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:14]([OH:23])=[O:36])(=[O:3])[CH3:2].[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 977OxygenHCID 6547AzobisisobutyronitrileHCID 67406CresatinHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 67406CresatinHCID 2386693-Acetoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 0.300 g of m-tolyl acetate, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to m-tolyl acetate), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4 H2O and 0.003 g of 2,2′-azobisisobutyronitrile 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 3-acetoxybenzoic acid in 75% yield at 78% conversion of m-tolyl acetate.

Sources & evidence

ORD record
ord-4d8e7e308f964d369e1c111544d0b5ee
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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