Methane, dichloromethoxy- → HCID 19047057, compound

HRID 1780615Notes

Reaction equation

HRID 1780615 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[C:7]([CH3:13])=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:4]=2[O:3]1.[CH3:15][O:16]C(Cl)Cl>ClCCl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[C:7]([CH3:13])=[C:8]([CH3:12])[C:9]([CH:15]=[O:16])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 19047070HCID 19047070, compound

Product 1

HCID 19047057HCID 19047057, compound

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 34.5 g of the 2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran in 200 ml of absolute dichloromethane was added 200 ml of titanium chloride (IV) and 18 ml of α,α-dichloromethyl methyl ether at 0° C. With stirring at room temperature for 45 minutes and refluxing for 15 minutes, the reaction mixture was quenched with 300 ml of water and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by recrystallization to afford 37.2 g of 2,3-dihydro-2,2,4,5,7-pentamethyl-benzofuran-6-carboxaldehyde as a white solid.

Workup

  1. temperaturerefluxing for 15 minutes
  2. customthe reaction mixture was quenched with 300 ml of water
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customFinal purification
  9. customwas carried by recrystallization

Sources & evidence

ORD record
ord-28b53685327d4b428ca714f85bce3f76
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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