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

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Reaction Steps

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.

Provenance & Evidence