Methane, dichloromethoxy- → HCID 19047059, compound

HRID 1780613Notes

Reaction equation

HRID 1780613 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[C:7]([CH3:12])=[CH:8][CH:9]=[C:10]([CH3:11])[C:4]=2[O:3]1.[CH3:14][O:15]C(Cl)Cl>ClCCl>[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[C:7]([CH3:12])=[C:8]([CH:14]=[O:15])[CH:9]=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 133338902,3-Dihydro-2,2,4,7-tetramethylbenzofuran

Product 1

HCID 19047059HCID 19047059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 110 g of the 2,3-dihydro-2,2,4,7-tetramethylbenzofuran in 500 ml of absolute dichloromethane was added 68.5 ml of titanium chloride(IV) and 56.5 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 1 l 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 104 g of 2,3-dihydro -2,2,4,7-tetramethyl-benzofuran-5-carboxaldehyde as a white solid.

Workup

  1. temperaturerefluxing for 15 minutes
  2. customthe reaction mixture was quenched with 1 l 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-8c9bdcb48d284f3ca461bebc2aca70b0
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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