Methyl Ethyl Ketone → HCID 59459897, compound

Participants

Reaction Conditions

Reaction Steps

In a separable flask having an inner volume of 300 ml, equipped with a reflux condenser, a stirrer, and a thermometer were charged 20.0 g (0.06 mol) of 2,2-bis(4-hydroxyphenyl)adamantane, 46 g (0.50 mol) of epichlorohydrin, 30 mL of MIBK, and 60 mL of DMSO, and the mixture was heated to 45° C. Then, 5.5 g (0.14 mol) of sodium hydroxide was added into this solution by small portions during a period of 1.5 hours. After completion of the addition, the reaction temperature was raised to 75° C., and the reaction was carried out for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, added by 25 mL of MIBK, and washed by water until the aqueous layer became neutral. The resulting organic layer was concentrated to obtain pale yellow solids. The pale yellow solids were dissolved in 285 g of MEK, added by 3.4 g of 25% by mass of aqueous sodium hydroxide solution, and then the mixture was stirred for 2 hours under reflux. Thereafter, the solution was cooled to room temperature, and washed by water until the aqueous layer became neutral from alkaline. The water-washing was performed two more times, and then the organic layer was concentrated. The resulting pale yellow solids were recrystallized by a mixed solvent of THF and isopropyl ether to obtain 23.2 g of 2,2-bis(4-glycidyloxyphenyl)adamantane having the following formula (96% purity by LC, epoxy equivalent of 224).

Provenance & Evidence