Acetic Acid → 4-Chlorobenzoic Acid

HRID 1182337Notes

Reaction equation

HRID 1182337 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.ON1C(=O)N(O)C(=O)N(O)C1=O.[C:21]([OH:24])(=[O:23])[CH3:22].O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:22]([C:21]([OH:24])=[O:23])=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 78104-ChlorotolueneHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 63184-Chlorobenzoic AcidHCID 78104-Chlorotoluene

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.380 g of 4-chlorotoluene, 0.027 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to 4-chlorotoluene), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4 H2O 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-chlorobenzoic acid in 99% yield at 100% conversion of 4-chlorotoluene.

Sources & evidence

ORD record
ord-4267d276d7ac4161bd5fa3d337e82f18
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

Loading…