Epichlorohydrin → HCID 59459894, compound

HRID 909686Notes

Reaction equation

HRID 909686 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[C:21]([CH3:27])[CH:20]=3)[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)=[CH:4][C:3]=1[CH3:28].[CH2:29]([CH:31]1[O:33][CH2:32]1)Cl.[OH-].[Na+].[CH2:36]1[CH2:40][O:39][CH2:38]C1>CO.CC(CC(C)=O)C.CS(C)=O>[CH2:29]([O:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]([C:9]2([C:19]3[CH:20]=[C:21]([CH3:27])[C:22]([O:26][CH2:36][CH:40]4[O:39][CH2:38]4)=[C:23]([CH3:25])[CH:24]=3)[CH:10]3[CH2:11][CH:12]4[CH2:13][CH:14]([CH2:15][CH:16]2[CH2:17]4)[CH2:18]3)=[CH:6][C:7]=1[CH3:8])[CH:31]1[O:33][CH2:32]1

Participants

8

Reactant 4

HCID 7835EpichlorohydrinHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21943944HCID 21943944, compound

Product 1

HCID 59459894HCID 59459894, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
45 °C

Procedure

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).

Workup

  1. customIn a separable flask having
  2. customan inner volume of 500 ml, equipped with a reflux condenser, a stirrer
  3. temperatureThen, the reaction temperature was raised to 65° C.
  4. customAfter completion of the reaction
  5. temperaturethe reaction solution was cooled to room temperature
  6. washwashed by water until the aqueous layer
  7. concentrationThe resulting organic layer was concentrated
  8. customto obtain a crude product as pale yellowish viscous liquid
  9. customto precipitate solids, which
  10. filtrationwere collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-df3d17bd5133432ea5e0ef4e91cac484
Source dataset
uspto-grants-2011_09
Patent number
US08017800B2

Reaction notes

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