Acrolein → 6-Hydroxychromene-3-carboxaldehyde

HRID 394695

Reaction equation

HRID 394695 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=O.[CH:11]([CH:13]=[CH2:14])=[O:12].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[OH:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:14][C:13]([CH:11]=[O:12])=[CH:4]2

Participants

6

Reactant 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 47708156-Hydroxychromene-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3 g (21.7 mmol) of 2,5-dihydroxybenzaldehyde and also 2.2 ml (32.6 mmol) of acrolein are added to a suspension of 6 g (43.5 mmol) of potassium carbonate in 50 ml of 1,4-dioxane; the medium is then heated at reflux for 12 hours. The salts are filtered off over Celite; the solvent is then evaporated in vacuo. The residue obtained is taken up in water; the aqueous phase is then extracted with ether. After drying over magnesium sulphate and evaporation of the solvent in vacuo, the crude product is triturated in dichloromethane to yield the title compound in the form of a yellow solid.

Workup

  1. temperaturethe medium is then heated
  2. temperatureat reflux for 12 hours
  3. filtrationThe salts are filtered off over Celite
  4. customthe solvent is then evaporated in vacuo
  5. customThe residue obtained
  6. extractionthe aqueous phase is then extracted with ether
  7. dry with materialAfter drying over magnesium sulphate and evaporation of the solvent in vacuo
  8. customthe crude product is triturated in dichloromethane

Sources & evidence

ORD record
ord-f05f9fe6aaf84aceb3adbcadbb4182a8
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Linked notes

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