Dichloromethane → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 1636578Notes

Reaction equation

HRID 1636578 reaction equation
ClCCl.[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1.[CH3:13][O:14]C(Cl)Cl>[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].O>[O:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]=[O:14])=[CH:12][C:7]=2[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 10329DihydrobenzofuranHCID 21004Methane, dichloromethoxy-

Product 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeYield 61,555.602%

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 962WaterSolvent

Procedure

Titanium chloride (28 ml) was dropwise added to a dichloromethane (100 ml) solution containing 2,3-dihydrobenzofuran (10.0 g, 83.2 mmols) and dichloromethyl methyl ether (11.3 ml, 0.125 mmols), while cooling with ice. The mixture was stirred for 1 hour, while still cooling with ice, and then water was added thereto. Dichloromethane was removed under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica-gel chromatography (hexane/ethyl acetate=1/1) to obtain 11.4 g (yield: 92%) of the target compound. This was oily.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile still cooling with ice
  3. customDichloromethane was removed under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified through silica-gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-24ef1c7affd142fb8af7bc2822e936e7
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

Loading…