Hydroquinone → Methacryloxymethyltrimethylgermane

Participants

Reaction Conditions

Reaction Steps

Approximately 225 ml of acetonitrile, 48 grams of potassium methacrylate, 2 grams of 18-crown-6 ether and 1 gram of hydroquinone was placed in a round bottom flask fitted with a condenser, stirrer, and septum inlet. The reaction mixture was heated to 80° C., using a heating mantle, and through the septum inlet approximately 45 grams of chloromethyltrimethyl germanium was added by syringe, in one aliquot. The reaction mixture was maintained for 65 hours at 80° C. with stirring. The reaction mixture was then cooled and filtered by vacuum suction through a fritted glass filter. The filtered solids were then washed with approximately 125 ml of acetonitrile and the wash filtrate combined with the first filtrate. The acetonitrile in the combined filtrate was removed by heating to 35° C. under vacuum. A 10:1 by volume mixture of n-hexane and methyl acetate was prepared. Approximately 50 ml of this mixture was added to the remaining reaction product. This combined mixture was then passed through a glass column containing 45 grams of silica adsorbent immersed in the n-hexane/methyl acetate mixture. The column was then washed with the n-hexane/methyl acetate mixture until IR analysis of the eluent showed no further trimethylgermylmethyl methacrylate. The n-hexane and methyl acetate present in the eluent were then removed under vacuum at 35° C. The remaining liquid was vacuum distilled at 4 mm Hg to yield pure trimethylgermylmethyl methacrylate (boiling point 58° C. at 4 mm Hg pressure).

Provenance & Evidence