Reaction of Chloromethyl Methyl Ether with Benzylmagnesium Chloride

Abstract

The reaction of the benzylmagnesium chloride with chloromethyl methyl ether has been studied in detail using various solvents. Five products have been obtained: 2-phenylethyl methyl ether [1], o-[2] and p-methylbenzyl methyl ether [3], and o-[4] and p-(2-methoxyethyl)benzyl methyl ether [5]. The results obtained show that the formation of abnormal products is suppressed with increase in solvent basicity and in the ionic character of the metal in the order of C-Li> C-Mg> C-Al. The intermediate responsible for the formation of diether [5] was characterized by trapping it through the reaction with gaseous formaldehyde.