N-Hydroxyphthalimide → Benzaldehyde

HRID 1532474Notes

Reaction equation

HRID 1532474 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ON1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2C1=O>C(#N)C>[CH:3](=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:15]([O:2][CH3:1])(=[O:16])[C:14]1[CH:13]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 10869Benzyl methyl ether2×

Product 2

HCID 240BenzaldehydeYield 52%HCID 7150Methyl BenzoateYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1 mmol of benzyl methyl ether, 0.1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile was stirred at 60° C. under a nitrogen monoxide atmosphere (1 atm) for 5 hours. Gas chromatographic analysis of products in the reaction mixture revealed that benzyl methyl ether was converted, at a rate of 78%, into benzaldehyde (yield: 52%), and methyl benzoate (yield: 20%).

Sources & evidence

ORD record
ord-7367bb857d2b434ab7a87bde2d22191f
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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