Water → 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde

HRID 466188Notes

Reaction equation

HRID 466188 reaction equation
[O:1]([C:8]1[CH:15]=[C:12]([CH:13]=O)[C:11]([OH:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:23]([CH:25]=[CH2:26])=[O:24].O>O1CCOCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:26][C:25]([CH:23]=[O:24])=[CH:13][C:12]=2[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7847AcroleinHCID 11430Potassium CarbonateHCID 149712582-Hydroxy-5-phenoxybenzaldehyde

Product 1

HCID 149712656-phenoxy-2H-1-benzopyran-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-phenoxysalicylaldehyde (15.0 g, 70.0 mmol, see example 2d) and potassium carbonate (19.4 g, 140.0 mmol) in 250 ml of 1,4-dioxane is treated with acrolein (4.32 g, 77.0 mmol) under nitrogen. The mixture is heated at reflux for 6 hours. Water is added and the mixture is extracted with dichloromethane. The organic layer is dried (MgSO4) and evaporated. The residue is purified by flash chromatography (silica gel, 10% EtOAc/hexane) to give 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde, as a fluorescent solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 6 hours
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialThe organic layer is dried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-6ea02f94213a4e928ef2fb095314ef05
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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