Water → 2-(3-nitrophenyl)-2-oxoacetaldehyde

HRID 1262446Notes

Reaction equation

HRID 1262446 reaction equation
[Se](=O)=O.O.[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)=[O:7].CC[O:19]C(C)=O>O1CCOCC1>[N+:14]([C:10]1[CH:9]=[C:8]([C:6](=[O:7])[CH:5]=[O:19])[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8494m-NitroacetophenoneHCID 8857Ethyl AcetateHCID 24007Selenium Dioxide

Product 1

HCID 3217362-(3-nitrophenyl)-2-oxoacetaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Selenium dioxide (9.4 g, 85 mmol) in 1,4-Dioxane (50.0 mL) and Water (1.70 mL, 94.4 mmol), was added 3-Nitroacetophenone (12.0 g, 72.9 mmol). The reaction mixture was refluxed for 4 hours with stirring, then taken up with EtOAc (100 mL) and washed with water (2×50 mL), brine (1×50 mL), dried over sodium sulfate, filtered and conc. in vacuo. Purification was by ISCO column chromatography (20-70% EtOAc/Hex) to afford (3-Nitro-phenyl)-oxo-acetaldehyde (9.98 g, 76%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. washwashed with water (2×50 mL), brine (1×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered and conc. in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-79c25afe20df44c69e7f4c0da3fd7ce7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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