Oxygen → Benzoic Acid

HRID 18859

Reaction equation

HRID 18859 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(ON1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2C1=O)(=[O:12])C.[O:25]=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:18]([OH:25])(=[O:19])[C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:16]=1.[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:12])[CH3:2].[C:4]1([C:1]([OH:12])([CH3:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 3

HCID 977OxygenHCID 7406CumeneHCID 2655661,3-dioxo-2,3-dihydro-1H-isoindol-2-yl acetate

Product 3

HCID 243Benzoic AcidHCID 7410AcetophenoneHCID 120532-Phenyl-2-propanol

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 1.202 g (10 mmol) of isopropylbenzene, 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, acetophenone and 2-phenyl-2-propanol in yields of 30%, 9% and 2% (analyzed by gas chromatography), respectively, with a conversion from isopropylbenzene of 65%.

Sources & evidence

ORD record
ord-c007daef6b9a4bf3b9fca14c572b554e
Source dataset
uspto-grants-2010_06
Patent number
US07741514B2

Linked notes

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