Oxygen → Acetophenone

HRID 2095225Notes

Reaction equation

HRID 2095225 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(CC)[CH3:2].C(#N)C.[OH:14]N1C(=O)C2=CC=CC=C2C1=O.O=O>C(OO)(CC)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 977OxygenHCID 6342AcetonitrileHCID 8680Sec-Butylbenzene2×HCID 10665N-Hydroxyphthalimide

Product 1

HCID 7410AcetophenoneYield 11%

Reagents, catalysts & solvents 1

HCID 1015400113020-06-9Solvent

Procedure

A solution of 10 mL of sec-butylbenzene (64.3 mmoles), 3.75 mL of acetonitrile and 0.64 mmoles of N-hydroxyphthalimide is stirred at 70° C. for 24 hours in an atmosphere of oxygen at a pressure of 1 bar. 1H-NMR analysis of the reaction mixture showed a secbutylbenzene conversion of 20% with a selectivity in sec-butyl hydroperoxide of 89% (result confirmed by iodometric titration) and 11% of acetophenone. The acetonitrile is removed by distillation and 0.57 mmoles of N-hydroxyphthalimide are recovered.

Sources & evidence

ORD record
ord-1639ac35c3044119ab46d81bd7495614
Source dataset
uspto-grants-2013_05
Patent number
US08445729B2

Reaction notes

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