Triethylamine → Adamantane

Participants

Reaction Conditions

Reaction Steps

A 200-mL glass reactor was equipped with a stirring device, a dropping funnel, and a temperature gauge. 10.0 g (42 mmol) of ADAMANTATE HM (manufactured by Idemitsu Kosan Co., Ltd.: 3-hydroxy-1-adamantyl methacrylate), 8.8 mL (63 mmol) of triethylamine, and 84.0 mL of toluene were added to the reactor, and the mixture was stirred while the reactor was immersed in a water bath at 25° C. 4.0 mL (50 mmol) of methanesulfonyl chloride were dropped to the mixture over 35 minutes, and the whole was stirred for an additional 25 minutes. 10 mL of water were added to the resultant to deactivate unreacted methanesulfonyl chloride. Part of the reaction liquid was taken and subjected to GPC measurement in such a manner that a production ratio between a target product and a polymer would be measured. The remaining reaction liquid was transferred to a 200-mL separating funnel, and the resultant was washed with 40 mL of water added to the resultant. After that, an organic layer was washed with 50 mL of 1-mmol/mL hydrochloric acid and then with 50 mL of water. No polymer was precipitated in the course of the liquid separating operation. 6.0 g (50 mmol) of anhydrous magnesium sulfate were added to the resultant, and the whole was dehydrated. After that, magnesium sulfate was removed by means of filtration. The filtrate was subjected to an evaporator in such a manner that toluene would be distilled off. After that, the temperature of the resultant viscous product was cooled to 0° C., followed by crystallization. After having been washed with a small amount of n-hexane, the crystal was separated by means of filtration, and was dried under reduced pressure until the amount of the crystal became constant, whereby an adamantane derivative as a target product (3-methanesulfonyloxy-1-adamantyl methacrylate) was obtained. Table 1 shows the results of: the yield (mol %) of the target product with respect to the adamantane compound as a raw material; the purity (mass %) of the target product measured by means of gas chromatography; and the production ratio (mass %) of the polymer as a result of the GPC measurement.

Provenance & Evidence