Dimethylformamide → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 1699743Notes

Reaction equation

HRID 1699743 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CN(C)[CH:12]=[O:13].P(Cl)(Cl)(Cl)=O>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10329DihydrobenzofuranHCID 24813Phosphorus oxychloride

Product 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2,3-dihydrobenzofuran (100.0 g, 832 mmols) in N,N-dimethylformamide (134.0 g, 1.83 mols) was added dropwise phosphorus oxychloride (255.1 g, 1.66 mols), then the mixture was stirred at 80-90° C. for 7.5 hours. The mixture was cooled to room temperature, poured into water (1 L) and stirred for 15 hours. The product was extracted with toluene (1.5 L). The extract was washed with water (500 mL) followed by a saturated aqueous solution of sodium bicarbonate (500 mL) and concentrated under reduced pressure to obtain 115.9 g (yield: 94%) of the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringstirred for 15 hours
  3. extractionThe product was extracted with toluene (1.5 L)
  4. washThe extract was washed with water (500 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bee52ff7d7b4254bdb29af8a3e6b1cb
Source dataset
uspto-grants-2002_02
Patent number
US06348485B1

Reaction notes

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