Benzofuran → 2-Benzofurancarboxaldehyde

HRID 236917Notes

Reaction equation

HRID 236917 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.P(Cl)(Cl)(Cl)=O.[C:15]([O-])(=[O:17])C.[Na+]>CN(C)C=O.O>[CH:8]1[CH:9]=[C:4]2[CH:3]=[C:2]([CH:15]=[O:17])[O:1][C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 9223BenzofuranHCID 24813Phosphorus oxychloride2×HCID 517045Sodium Acetate

Product 1

HCID 613412-Benzofurancarboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of benzofuran (163 g, 1.39 mole) in dimethylformamide (264 g, dried over magnesium sulfate overnight) in a 2-1, 3-necked flask was stirred and treated dropwise with phosphorus oxychloride (233 g, 136 ml). The solution was heated and stirred on a steam bath for 8 hrs. Another 88 g of dry dimethylformamide, followed by 70 g (42 ml) of phosphorus oxychloride, was added and the heating and stirring were continued overnight. After cooling, the solution was slowly poured into a stirred solution of 260 g of sodium acetate in 1500 ml of water. The solution was extracted four times with 500 ml of ether. The ether extracts were washed with dilute aqueous sodium hydroxide solution and then with water. The solution was then dried over magnesium sulfate and filtered.

Workup

  1. temperatureThe solution was heated
  2. additionwas added
  3. stirringthe heating and stirring
  4. waitwere continued overnight
  5. temperatureAfter cooling
  6. extractionThe solution was extracted four times with 500 ml of ether
  7. washThe ether extracts were washed with dilute aqueous sodium hydroxide solution
  8. dry with materialThe solution was then dried over magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-1bcdb192cff44481a8342d58cbfec645
Source dataset
uspto-grants-1979_06
Patent number
US04159274

Reaction notes

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