Methyl Ethyl Ketone → HCID 24888073, compound

Participants

Reaction Conditions

Reaction Steps

In a separable flask having an inner volume of 300 ml, equipped with a reflux condenser, a stirrer, a thermometer, and a nitrogen inlet were charged 30 mL of MIBK, 60 mL of DMSO, and 65 g (0.70 mol) of epichlorohydrin, and the atmosphere of the system was displaced by nitrogen. Then, 20.6 g (0.09 mol) of 1-(2,4-dihydroxyphenyl)adamantane was added and the mixture was heated to 45° C. with stirring. Then, 7.6 g (0.19 mol) of sodium hydroxide was added into this solution by small portions during a period of 0.5 hour, and the agitation was continued for further 2 hours. Thereafter, 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 viscous liquid having a pale yellow color. The viscous liquid having a pale yellow color was 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 to obtain 28.3 g of 1-(2,4-diglycidyloxyphenyl)adamantane having the following formula (93% purity by LC, epoxy equivalent of 185).

Provenance & Evidence