Methane, dichloromethoxy- → 2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde

HRID 1780608Notes

Reaction equation

HRID 1780608 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[C:7]([CH3:13])=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:4]=2[O:3]1.[CH3:15][O:16]C(Cl)Cl>ClCCl>[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[C:7]([CH3:13])=[C:8]([CH3:12])[C:9]([CH3:11])=[C:10]([CH:15]=[O:16])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 190785652,2,4,5,6-Pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 190470682,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 22 g of the 2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran in 150 ml of absolute dichloromethane was added 12.8 ml of titanium chloride(IV) and 15.8 ml of a α,α-dichloromethyl methyl ether at 0° C. With stirring at room temperature for 1 hour, 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 20 g of 2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde as a white solid.

Workup

  1. customthe reaction mixture was quenched with 300 ml of water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b74dd7b2c84c49c58140a587605c1bfd
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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