Water → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 420898Notes

Reaction equation

HRID 420898 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>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10329DihydrobenzofuranHCID 24813Phosphorus oxychloride

Product 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeYield 275.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

2,3-Dihydrobenzofuran (100 g, 832 mmol) and N,N-dimethylformamide (134 g, 1830 mmol) were mixed and heated, and phosphorus oxychloride (255 g, 1643 mmol) were added thereto at an inner temperature of 70 to 80° C. over 2 hrs. The reaction mixture was heated at an inner temperature of 80 to 90° C. and stirred for 7.5 hrs. Then, the resulting mixture was added dropwise to water (1000 g) under cooling, and stirred at room temperature for 5 hrs. The resulting mixture was extracted with toluene, and the extract was washed sequentially with water, saturated sodium bicarbonate aqueous solution and water, and the organic layer was concentrated under vacuum to give a toluene solution of the title compound (amount 340 g, apparent yield 100%).

Workup

  1. temperatureheated
  2. temperatureunder cooling
  3. stirringstirred at room temperature for 5 hrs
  4. extractionThe resulting mixture was extracted with toluene
  5. washthe extract was washed sequentially with water, saturated sodium bicarbonate aqueous solution and water
  6. concentrationthe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-0f71df6a58ff4a39af6ff7400a9d310a
Source dataset
uspto-grants-2012_01
Patent number
US08097737B2

Reaction notes

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