Sodium Hydroxide → N-[(4-Methoxyphenyl)methylidene]hydroxylamine

HRID 1742522Notes

Reaction equation

HRID 1742522 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:12][OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 25 g (0.18 mol) of 4-methoxybenzaldehyde in 100 ml of ethanol was added dropwise under ice cooling to a solution of 15.3 g (0.22 mol) of hydroxylamine hydrochloride and 11.0 g (0.28 mol) of sodium hydroxide in 100 ml of water. After completion of the dropwise addition, the resulting mixture was stirred at room temperature for 30 minutes and ethanol was distilled off under reduced pressure. An insoluble solid was then collected by filtration. The solid was washed with water and hexane. The washings were combined with the filtrate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off, whereby 4-methoxybenzaldoxime was obtained as a colorless liquid. Its yield was 23.7 g (85%). It was then provided for the next reaction without further purification.

Workup

  1. additionAfter completion of the dropwise addition
  2. distillationethanol was distilled off under reduced pressure
  3. filtrationAn insoluble solid was then collected by filtration
  4. washThe solid was washed with water and hexane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4961a8d7a22f444a8ddac192a5761420
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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