Methane, dichloromethoxy- → HCID 19047057, compound

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

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.