2-Acetylbenzofuran → 2-Benzofuranglyoxylaldehyde

HRID 1759575Notes

Reaction equation

HRID 1759575 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[Se](=O)=[O:14].O1CCOCC1>O.CN(C)C=O>[O:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=[C:4]1[C:1](=[O:3])[CH:2]=[O:14]

Participants

6

Reactant 3

HCID 154352-AcetylbenzofuranHCID 24007Selenium DioxideHCID 312751,4-Dioxane

Product 1

HCID 189261632-BenzofuranglyoxylaldehydeYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-acetylbenzofuran (100 g) and selenium dioxide (69.3 g) was dissolved in water (20 ml) and dioxan (500 ml) and heated under reflux for 24 h. The reaction mixture was filtered and the solvent evaporated to give a dark-red solid which was taken up in dimethylformamide and heated on a steam bath for 8 h. The solution was filtered, the solvent evaporated and the residue triturated with ether to give the title compound (65.4 g).

Workup

  1. temperatureunder reflux for 24 h
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated
  4. customto give a dark-red solid which
  5. temperatureheated on a steam bath for 8 h
  6. filtrationThe solution was filtered
  7. customthe solvent evaporated
  8. customthe residue triturated with ether

Sources & evidence

ORD record
ord-8aad654f36964d799bec74c57f61312b
Source dataset
uspto-grants-1982_07
Patent number
US04341793

Reaction notes

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