Methacryloyl chloride → 2-Ethyl-2-methacryloyloxyadamantane

Participants

Reaction Conditions

Reaction Steps

To 31.1 g of 2-adamantanone was added 50 g of diethyl ether to form a solution. To the solution was added dropwise 200 ml of a solution of ethyllithium (at a concentration of 1.14 mol/L) in diethyl ether while keeping the solution at a temperature not higher than 10° C. After stirring for two hours at 0° C., methacrylic acid chloride in an amount of 26.2 g (1.2 times the molar amount of 2-adamantanone) was added dropwise to the solution while keeping the solution at a temperature not higher than 10° C. After the dropwise addition was completed, the resulting mixture was stirred for about 12 hours at room temperature. Thereafter, the precipitated organic salt was filtered off. The resulting organic layer was washed with anqueous solution of 5 wt % sodium bicarbonate and then washed with water twice. The organic layer was concentrated and then distilled under reduced pressure to obtain 2-ethyl-2-adamantyl methacrylate represented by the following formula.

Provenance & Evidence