Acetic Acid → P-Toluic Acid

HRID 18849

Reaction equation

HRID 18849 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4]C(C)=[CH:6][CH:7]=1.C(ON1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2C1=O)(=O)C.[O:24]=O.[C:26]([OH:29])(=[O:28])[CH3:27]>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:17]([OH:18])(=[O:24])[C:16]1[CH:15]=[CH:22][C:21]([C:26]([OH:29])=[O:28])=[CH:20][CH:19]=1.[CH3:1][C:2]1[CH:7]=[CH:6][C:27]([C:26]([OH:29])=[O:28])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 7809P-XyleneHCID 2655661,3-dioxo-2,3-dihydro-1H-isoindol-2-yl acetate

Product 2

HCID 7470P-Toluic AcidHCID 7489Terephthalic Acid

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

A mixture of 2 mmol of p-xylene, 0.4 mmol of N-acetoxyphthalimide, 0.01 mmol of cobalt(II) acetate and 5 ml of acetic acid was stirred at 100° C. in an atmosphere of oxygen gas (1 atm=0.1 MPa) for 14 hours and thereby yielded terephthalic acid and p-toluic acid in yields of 91% and 1%, respectively.

Sources & evidence

ORD record
ord-d7a2676f29ef4003b0cbcc84febbd0a6
Source dataset
uspto-grants-2010_06
Patent number
US07741514B2

Linked notes

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