Water → 2-Furanacetaldehyde, alpha-oxo-, hydrate

HRID 248479Notes

Reaction equation

HRID 248479 reaction equation
[Se](=O)=O.[OH2:4].[C:5]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)(=[O:7])[CH3:6]>O1CCOCC1>[O:7]=[C:5]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)[CH:6]=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 145052-AcetylfuranHCID 24007Selenium Dioxide

Product 1

HCID 1463252-Furanacetaldehyde, alpha-oxo-, hydrate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 55 g of selenium dioxide, 11 ml of water and 150 ml of dioxane was heated at 55° C. until solution was complete. A 55 g portion of 2-acetylfuran was added, the mixture was refluxed for 4 hours, then filtered and evaporated. The residue was dissolved in dichloromethane, treated with activated charcoal, filtered and evaporated. The residue was distilled, giving 28 g of α-oxo-2-furanacetaldehyde.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. additiontreated with activated charcoal
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-54d3d67547554281ba8a55eb53a0c3b8
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…