Ethyl Bromide → 2-Ethyl-2-methacryloyloxyadamantane

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Reaction Steps

15 g (0.1 mol) of 2-adamantanone obtained in Example 3 was dissolved in 50 ml of tetrahydrofuran, and 12 g (0.11 mol) of ethyl bromide was added to the resulting solution. 0.1 g of metal lithium was added to the solution each time until the total amount became 1.3 g (0.19 mol) in such a manner that the temperature of the solution should not exceed 30° C. while they were violently stirred. After the proceeding of a reaction was checked by gas chromatography and it was confirmed visually that the metal lithium disappeared, 10 g (0.1 mol) of methacrylic acid chloride was added to the reaction solution. After it was confirmed by gas chromatography that the reaction proceeded to the full, 3 ml of methanol and 3 ml of a 5% aqueous solution of sodium hydroxide were added to the reaction solution and stirred at room temperature for 1 hour to stop the reaction. Thereafter, the organic solvent was distilled off under reduced pressure, 200 ml of hexane was added, and the obtained solution was washed with a 10% aqueous solution of sodium hydroxide and 20% brine sequentially. Thereafter, hexane was distilled off under reduced pressure to obtain a crude product which was then recrystallized in isopropanol to obtain 7.2 g (0.029 mol, 29%) of 2-ethyl-2-adamantyl methacrylate.

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