Benzaldehyde → O-benzylbenzaldoxime

HRID 1954748Notes

Reaction equation

HRID 1954748 reaction equation
C(O)C.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:11]([O:18][NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH2:11]([O:18][N:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 11430Potassium CarbonateHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 561973O-benzylbenzaldoximeYield 119%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethanol (100 mL), potassium carbonate (8.98 g, 65 mmol), and O-benzylhydroxylamine hydrochloride (10.0 g, 62.7 mmol) was added benzaldehvde (6.65 g, 62.7 mmol). The mixture was refluxed for 5 hours, allowed to cool to room temperature, and diluted with water (500 mL). The aqueous solution was extracted with ethyl acetate (500 mL). The organic layer was washed with water, dried over magnesium sulfate, filtered, and concentrated by rotary evaporation to give the title compound as a yellow oil (14.96 g, 119%).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. extractionThe aqueous solution was extracted with ethyl acetate (500 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-83f29f4bfb02481ebc55d3e3b9d72fb5
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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