Water → Methyl 1-(4-chloromethylphenyl)cyclopropanecarboxylate

Participants

Reaction Steps

To a solution of methyl 1-phenylcyclopropanecarboxylate (8.5 g) in methylene chloride (70 ml) was added titanium tetrachloride (8.0 ml) under ice-cooling. To this solution was added dropwise a solution of methoxymethyl chloride (5.5 ml) in methylene chloride (30 ml) under ice-cooling. The mixture was stirred at room temperature for 5 hr and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a pale-brown oil. The oil was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (7.9 g) as a colorless oil.

Provenance & Evidence