Methane, dichloromethoxy- → 3-Formyl-4-methoxyphenyl methyl carbonate

Participants

Reaction Steps

Under an argon atmosphere, to a solution of 4-methoxyphenyl methyl carbonate (10.0 g) in dichloromethane (125 mL) was added a solution of titanium (IV) chloride (14.3 mL) in dichloromethane (25 mL) at 0° C., and then dichloro(methoxy)methane (5.8 mL) was added dropwise over 30 min. The reaction mixture was warmed to room temperature, and stirred for 30 min. Dichloromethane (about 70 mL) was evaporated, and ice (120 g) and 12N hydrochloric acid were added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (10.5 g) as a yellow oil. This compound was used for the next step without further purification.

Provenance & Evidence