Acrolein → 6-Hydroxychromene-3-carboxaldehyde

HRID 466174Notes

Reaction equation

HRID 466174 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].[CH:17]([CH:19]=[CH2:20])=[O:18]>O1CCOCC1>[OH:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][CH2:20][C:19]([CH:17]=[O:18])=[CH:4][C:3]=2[CH:6]=1

Participants

5

Reactant 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 47708156-Hydroxychromene-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The starting material is prepared as follows: 2,5-Dihydroxybenzaldehyde (25.0 g, 0.18 mol) is dissolved in 375 ml of 1,4-dioxane. To this is sequentially added potassium carbonate (50.0 g, 0.36 mol) and acrolein (15.22 g, 0.27 mol). The mixture is heated at reflux overnight, cooled, and partitioned between water and ether. The aqueous layer is removed and extracted twice with ether. The combined organic layers are dried (MgSO4) and evaporated. Trituration of the residue with dichloromethane, followed by filtration and drying, yields 6-hydroxy-2H-1-benzopyran-3-carboxaldehyde, m.p. 163°-165° C., as a yellow crystalline solid.

Workup

  1. customThe starting material is prepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux overnight
  4. temperaturecooled
  5. custompartitioned between water and ether
  6. customThe aqueous layer is removed
  7. extractionextracted twice with ether
  8. dry with materialThe combined organic layers are dried (MgSO4)
  9. customevaporated
  10. filtrationTrituration of the residue with dichloromethane, followed by filtration
  11. customdrying

Sources & evidence

ORD record
ord-763ad5d4fe4f4ca6b62819782459a78d
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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