N-Hydroxyphthalimide → Hydroperoxide, phenylmethyl

HRID 23829

Reaction equation

HRID 23829 reaction equation
ON1C(=O)[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[O-:13]O.C1(C(C)C)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:3]([O:12][OH:13])[C:4]1[CH:5]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 53627471Cumen hydroperoxide

Product 1

HCID 6451509Hydroperoxide, phenylmethyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.3 mmol of N-hydroxyphthalimide and 0.6 mmol of cumene hydroperoxide are added at a temperature of 125° C. to 30 mmol of toluene in a round-bottomed flask having an attached reflux condenser. The reaction mixture is stirred for 8 hours at said temperature under an oxygen atmosphere of 1 bar. Benzyl hydroperoxide is obtained at a selectivity of 51.7% at a toluene conversion rate of 8%. Other products are benzaldehyde (24.6%) and benzoic acid (23.6%).

Workup

  1. temperaturean attached reflux condenser

Sources & evidence

ORD record
ord-7f450eba77dc4cb2b2f224ef056837d4
Source dataset
uspto-grants-2005_02
Patent number
US06852893B2

Linked notes

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