N-Hydroxyphthalimide → Benzaldehyde

HRID 1532475Notes

Reaction equation

HRID 1532475 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2].[OH:11]N1C(=O)C2=CC=CC=C2C1=O>C(#N)C>[CH:4](=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:4]([O:3][CH2:1][CH3:2])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 10873Benzyl ethyl ether2×

Product 2

HCID 240BenzaldehydeYield 57%HCID 7165Ethyl benzoateYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1 mmol of benzyl ethyl 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 ethyl ether was converted, at a rate of 82%, into benzaldehyde (yield: 57%), and ethyl benzoate (yield: 18%).

Sources & evidence

ORD record
ord-205e82f1af7b47aeb064f0a03b1cb203
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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