Epichlorohydrin → HCID 23113189, compound

HRID 2355800Notes

Reaction equation

HRID 2355800 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3]C1.[OH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([CH2:18][OH:19])([CH2:11]3)[CH2:9]1)[CH2:15]2.[H-].[Na+].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>C(Cl)(Cl)Cl>[CH2:22]([O:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][C:10]([CH2:18][O:19][CH2:3][CH:4]4[O:1][CH2:5]4)([CH2:16]3)[CH2:9]1)[CH2:17]2)[CH:24]1[O:26][CH2:25]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 703011[3-(Hydroxymethyl)-1-adamantyl]methanol

Product 1

HCID 23113189HCID 23113189, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

300 ml of dehydrated tetrahydrofuran containing 19.6 g (0.1 mol) of 1,3-bis(hydroxymethyl)adamantane 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, followed by washing with water. The chloroform layer was dried with magnesium sulfate. The dried chloroform layer was subjected to distillation under reduced pressure for solvent removal, whereby was obtained a white solid and oily matter.

Workup

  1. washby washing with water
  2. dry with materialThe chloroform layer was dried with magnesium sulfate
  3. distillationThe dried chloroform layer was subjected to distillation under reduced pressure for solvent removal
  4. customwhereby was obtained a white solid and oily matter

Sources & evidence

ORD record
ord-5772540f082e4804b2a7718f9593e7bf
Source dataset
uspto-grants-2010_07
Patent number
US07754903B2

Reaction notes

Loading…