반응 #996865

반응 방정식

sodium hydroxide

1,3-bis(4-hydroxyphenyl)adamantane

epichlorohydrin

MEK

sodium hydroxide

→

1,3-bis(4-glycidyloxyphenyl)adamantane

수율 92.9%

용매

DMSO

MIBK

MIBK

반응 조건

후처리

1. 1
   기타In a separable flask having
2. 2
   기타an inner volume of 300 ml, equipped with a reflux condenser, a stirrer
3. 3
   workup.ADDITIONAfter completion of the addition
4. 4
   온도the reaction temperature was raised to 75° C.
5. 5
   온도the mixture was cooled to room temperature
6. 6
   세척washed with water until the aqueous layer
7. 7
   농축The resulting organic layer was concentrated
8. 8
   기타to obtain pale yellow solids
9. 9
   온도under reflux
10. 10
    온도Thereafter, the solution was cooled to room temperature
11. 11
    세척washed by water until the aqueous layer
12. 12
    세척The water-washing
13. 13
    농축the organic layer was concentrated
14. 14
    기타to obtain pale yellow solids, which
15. 15
    기타was recrystallized by a mixed solvent of THF (tetrahydrofuran) and isopropyl ether

실험 절차

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 1,3-bis(4-hydroxyphenyl)adamantane, 46 g (0.50 mol) of epichlorohydrin, 30 mL of MIBK, and 60 mL of DMSO, and they were 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 mixture was cooled to room temperature, added by 25 mL of MIBK, and washed with 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 to obtain pale yellow solids, which was recrystallized by a mixed solvent of THF (tetrahydrofuran) and isopropyl ether to obtain 24.1 g of 1,3-bis(4-glycidyloxyphenyl)adamantane having the following formula (purity of 94% by LC (liquid chromatography), epoxy equivalent of 224).

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