Ethanol → Ethyl 5-formylfuran-2-carboxylate

HRID 1432270Notes

Reaction equation

HRID 1432270 reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=[O:2].[CH2:11](O)[CH3:12].S(=O)(=O)(O)O>O>[CH:1]([C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27937195-Formyl-2-furancarboxylic Acid

Product 1

HCID 15589950Ethyl 5-formylfuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-formyl-2-furancarboxylic acid (0.5 g),in ethanol (35 ml), sulfuric acid (3.5 ml) was added at 0° C. and the mixture was heated under reflux for 5 hours. After cooling, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.5316 g of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was separated

Sources & evidence

ORD record
ord-6dc32894473140bfa517ff7fc5080a83
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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