2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Benzofuran-7-carbaldehyde

HRID 1107867Notes

Reaction equation

HRID 1107867 reaction equation
[CH:1]([C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+]>O1CCOCC1>[CH:1]([C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehyde

Product 1

HCID 111264061-Benzofuran-7-carbaldehydeYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.950 g (6.4 mmol) of 7-formyl-2,3-dihydrobenzofuran, 1.82 g (8 mmol) of 2,3-dichloro-5,6-dicyanocyclohexa-2,5-diene-1,4-dione (DDQ) and 30 ml of dioxane are introduced into a 100 ml three-necked flask equipped with a reflux condenser. Heating is carried out at reflux for 24 hours. 100 ml of a molar sodium hydroxide solution are added and extraction is carried out with ethyl ether (3×80 ml). The organic phases are combined, dried and concentrated under vacuum. The residue is purified by silica flash chromatography (elution: 5% ethyl acetate in petroleum ether). 215 mg of 7-formylbenzofuran are obtained in the form of a yellow oil (Yield: 23%).

Workup

  1. customequipped with a reflux condenser
  2. temperatureHeating
  3. temperatureat reflux for 24 hours
  4. extractionextraction
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by silica flash chromatography (elution: 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5e875af04a314fbaae64cec816a1560f
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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