Methyl Ethyl Ketone → HCID 24888073, compound

Participants

Reaction Conditions

Reaction Steps

Into a separable flask having an inner volume of 300 ml and equipped with a reflux condenser, a stiffer, a thermometer, and a nitrogen inlet were charged 30 ml of MIBK, 60 ml of DMSO, and 65 g (0.70 mol) of epichlorohydrin. After the atmosphere was displaced with nitrogen, 20.6 g (0.09 mol) of 1-(2,4-dihydroxyphenyl)adamantane synthesized in the above (1) was added and the mixture was heated to 45° C. with agitation. Into this solution, 7.6 g (0.19 mol) of sodium hydroxide was added over 0.5 hour, and the agitation was continued for another 0.5 hour. Then the temperature was raised to 65° C. and the agitation was continued for 2 hours. The reaction solution was cooled to room temperature, added with 25 ml of MIBK, and washed by water until the aqueous phase became neutral, and then the organic layer was concentrated to obtain yellowish viscous solution. The yellowish viscous solution was dissolved into 285 g of MEK, added with 3.4 g of 25% by mass of aqueous sodium hydroxide solution, and then heated under reflux with agitation for 2 hours. The solution was cooled to room temperature, washed with water until the aqueous phase became neutral from alkaline, and then the washing was done for two more times. The organic layer was concentrated to obtain the target compound (yield 94%). The LC (liquid chromatography) of this compound showed the purity of 95% (monomer content was 95% and the rests were oligomers of the target compound).

Provenance & Evidence