Oxygen → Benzoic Acid

HRID 18857

Reaction equation

HRID 18857 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].C(ON1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2C1=O)(=[O:11])C.[O:24]=O>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C(O)(=O)C>[C:17]([OH:24])(=[O:18])[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:15]=1.[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:11])[CH3:2]

Participants

8

Reactant 3

HCID 977OxygenHCID 7500EthylbenzeneHCID 2655661,3-dioxo-2,3-dihydro-1H-isoindol-2-yl acetate

Product 2

HCID 243Benzoic AcidHCID 7410Acetophenone

Reagents, catalysts & solvents 3

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 93021Manganese acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.062 g (10 mmol) of ethylbenzene, 0.205 g (1 mmol) of N-acetoxyphthalimide, 0.025 g (0.1 mmol) of cobalt(II) acetate tetrahydrate, 0.025 g (0.1 mmol) of manganese(II) acetate tetrahydrate and 15 ml of acetic acid was stirred at 100° C. in an atmosphere of oxygen gas (1 atm=0.1 MPa) for 8 hours and thereby yielded benzoic acid and acetophenone in yields of 86% and 5% (analyzed by gas chromatography), respectively, with a conversion from ethylbenzene of 99%.

Sources & evidence

ORD record
ord-163b98d0cf274b998304db158ea3a940
Source dataset
uspto-grants-2010_06
Patent number
US07741514B2

Linked notes

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