Benzoic Acid → Acetophenone

HRID 18858

Reaction equation

HRID 18858 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].C(ON1C(=O)C2=CC=CC=C2C1=O)(=[O:11])C.C(O)(=O)C1C=CC=CC=1>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:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:11])[CH3:2]

Participants

7

Reactant 3

HCID 243Benzoic AcidHCID 7500Ethylbenzene2×HCID 2655661,3-dioxo-2,3-dihydro-1H-isoindol-2-yl acetate

Product 1

HCID 7410AcetophenoneYield 85%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

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 130° C. in an atmosphere of air [2 MPa (gauge pressure)] for 8 hours and thereby yielded benzoic acid in a yield of 85% (analyzed by gas chromatography) with a conversion from ethylbenzene of 96%. In this procedure, acetophenone was not produced.

Sources & evidence

ORD record
ord-0ed1deefb693476d8324060234940cbd
Source dataset
uspto-grants-2010_06
Patent number
US07741514B2

Linked notes

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