Water → 4-Nitrophenylglyoxal

HRID 619327Notes

Reaction equation

HRID 619327 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[Se].[OH2:14]>>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2]([CH:1]=[O:14])=[O:3])=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 962WaterHCID 7487p-NitroacetophenoneHCID 6326970Selenium

Product 1

HCID 1512424-Nitrophenylglyoxal

Procedure

6.60 (40 mmol) 4-nitroacetophenone was dissolved in 30 ml of diozane and 5 g, (45 mmol) selenium dioxyde was dissolved in 2.2 ml water and mixed. The mixture was refluxed for 16 hours with continuous stirring. The reaction mixture was passed through an alumina column to remove selenium. The solvent was evaporated in vacuum. The crude product was used in the next step without further purification. Rf 0.80(EtOAc) Y:7.00 (85%) IR(cm-1): 1730 (CO), 1520, 1330 (NO2)

Workup

  1. additionmixed
  2. temperatureThe mixture was refluxed for 16 hours with continuous stirring
  3. customto remove selenium
  4. customThe solvent was evaporated in vacuum
  5. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-0e0a1dfaa2c1413b93db858efd8e557b
Source dataset
uspto-grants-1999_09
Patent number
US05958959

Reaction notes

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