クロロ酢酸エステルとエチレンオキシドの反応による2-クロロエトキシ酢酸エステルの合成

概要

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The synthetic reaction of alkyl chloroacetates (1) with ethylene oxide (EO) in N, N-dimethylacet-amide (DMA) was studied. EO was inserted into the C-Cl bond of t-butyl, hexyl, octyl, 1-methyl-heptyl and decyl chloroacetates to form novel compounds, alkyl 2-chloroethoxyacetates (2), although the insertion of EO into the C-Cl bond of 1-chlorooctane did not occur under the same conditions. Zinc chloride and lithium halide were effective catalysts in the present reaction. Optimum amounts of DMA and of zinc chloride to (1) were equimolar and 1/30-1/10 molar, respectively, and optimum temperature was at 110120°C. The effect of the structure of alkyl group of (1) on the yield of (2) was studied. The branching and increasing of alkyl chain diminished the yield of (2).
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