Dichloromethane → 7-Chloro-2,2,4,5-tetramethyl-2,3-dihydro-1-benzofuran

HRID 1780602Notes

Reaction equation

HRID 1780602 reaction equation
Cl[C:2]1C=C(C)C(C)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([CH3:18])=[CH:13][C:12]=1[Cl:19].[Al+3].[Cl-].[Cl-].[Cl-].Cl[CH2:25]Cl>>[Cl:19][C:12]1[C:11]2[O:10][C:3]([CH3:2])([CH3:4])[CH2:25][C:16]=2[C:15]([CH3:17])=[C:14]([CH3:18])[CH:13]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 54562905HCID 54562905, compound

Product 1

HCID 152683107-Chloro-2,2,4,5-tetramethyl-2,3-dihydro-1-benzofuran

Procedure

To a solution of 23.8 g of the methally 2-chloro-4,5-dimethylphenyl ether in 200 ml absolute dichloromethane at -70° C. was added 10 g of AlCl3 under a current of nitrogen gas. After stirring and warming to the room temperature over a period of 1 hour, the reaction mixture was added 200 ml of ice-water and the aqueous layer was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 20 g of 7-chloro-2,3-dihydro-2,2,4,5-tetramethylbenzofuran as yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford a crude product
  7. customFinal purification

Sources & evidence

ORD record
ord-385b5925f06846cb98e45610bf2ae99f
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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