Epichlorohydrin → HCID 13980937, compound

HRID 2355799Notes

Reaction equation

HRID 2355799 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3]C1.[C:6]12([OH:17])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2.[H-].[Na+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>C(Cl)(Cl)Cl>[CH2:20]([O:17][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([O:16][CH2:3][CH:4]4[O:1][CH2:5]4)([CH2:9]3)[CH2:7]1)[CH2:13]2)[CH:22]1[O:24][CH2:23]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5738291,3-Adamantanediol

Product 1

HCID 13980937HCID 13980937, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

300 ml of dehydrated tetrahydrofuran containing 16.8 g (0.1 mol) of 1,3-adamantanediol and 5.3 g (0.22 mol) of sodium hydride was stirred in a nitrogen atmosphere at the reflux temperature for 2 hours. Thereto was dropwise added 20.4 g (0.22 mol) of epichlorohydrin, followed by stirring at the reflux temperature for 12 hours. To the reaction mixture was added 200 ml of chloroform. The chloroform layer was washed with water and dried with magnesium sulfate. The dried chloroform layer was subjected to distillation under reduced pressure for solvent removal, to obtain oily matter. It was purified by silica gel column chromatography to obtain 1.79 g (yield: 6.4%) of oily matter.

Workup

  1. washThe chloroform layer was washed with water
  2. dry with materialdried with magnesium sulfate
  3. distillationThe dried chloroform layer was subjected to distillation under reduced pressure for solvent removal
  4. customto obtain oily matter
  5. customIt was purified by silica gel column chromatography
  6. customto obtain 1.79 g (yield: 6.4%) of oily matter

Sources & evidence

ORD record
ord-4cbce698445a4fe7bf14ad634da2365a
Source dataset
uspto-grants-2010_07
Patent number
US07754903B2

Reaction notes

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