Methane, dichloromethoxy- → 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 mmol of 3,5-dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester and 6 mmol of dichloromethyl methyl ether was taken in 8 mL of dichloromethane. The mixture was cooled to −78° C. under stirring, and then titanium tetrachloride (6 mmol) in dichloromethane (4 ml) was added dropwise over 0.5 h. Upon completion, the reaction mixture was poured into ice-cold water and partitioned. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over MgSO4, and the solvent was evaporated by a rotary evaporator. The residue was purified by column chromatography to afford 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (60%).

Provenance & Evidence