Epichlorohydrin → HCID 59459894, compound

Participants

Reaction Conditions

Reaction Steps

In a separable flask having an inner volume of 500 ml, equipped with a reflux condenser, a stirrer, and a thermometer were charged 50.2 g (0.13 mol) of 2,2-bis(4-hydroxy-3,5-dimethylphenyl)adamantane, 99.6 g (1.06 mol) of epichlorohydrin, 75 mL of MIBK, and 150 mL of DMSO, and the mixture was heated to 45° C. Then, 13.2 g (0.33 mol) of sodium hydroxide was added into this solution by small portions during a period of 1.0 hour. Then, the reaction temperature was raised to 65° C., and the reaction was carried out for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, added by 250 mL of MIBK, and washed by water until the aqueous layer became neutral. The resulting organic layer was concentrated to obtain a crude product as pale yellowish viscous liquid. After the crude product was dissolved in 70 mL of THF, the resulting solution was added drop-wisely into 350 mL of methanol to precipitate solids, which were collected by filtration and dried to obtain 60.5 g of 2,2-bis(4-glycidyloxy-3,5-dimethylphenyl)adamantane having the following formula (94% purity by LC, epoxy equivalent of 259).

Provenance & Evidence