(-)-Epichlorohydrin → Diglycidyl ether

HRID 1074122Notes

Reaction equation

HRID 1074122 reaction equation
C(C1C=CC(C2[CH:20]=[CH:19][C:18]([OH:21])=C(C#N)C=2)=CC=1)CCCCCCC.[CH3:24][C:25](C)([O-:27])[CH3:26].[K+].C1[O:32][C@H]1CCl>C(O)(C)(C)C.CN(C1C=CN=CC=1)C>[CH2:24]([O:32][CH2:20][CH:19]1[O:21][CH2:18]1)[CH:25]1[O:27][CH2:26]1

Participants

6

Reactant 3

HCID 2734062(-)-EpichlorohydrinHCID 189501194-(4-n-Octylphenyl)-2-cyanophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-(4-n-octylphenyl)-2-cyanophenol (1.9 g) prepared in Preparation 2 in t-butyl alcohol (40 ml) is added potassium t-butoxide (832 mg). After a short period of time, R-(-)-epichlorohydrin (2.5 ml) and 4-(N,N-dimethylamino)pyridine (100 mg) are added to the mixture, and the mixture is stirred at room temperature for 2 days. The reaction mixture is concentrated under reduced pressure, and to the residue is added water. The mixture is extracted with ether and the extract is dried and distilled to remove ether. The crude product thus obtained is purified by silica gel column chromatography to give S isomer of a glycidyl ether (750 mg) of the following formula: ##STR49##

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionto the residue is added water
  3. extractionThe mixture is extracted with ether
  4. customthe extract is dried
  5. distillationdistilled
  6. customto remove ether
  7. customThe crude product thus obtained
  8. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9874e7dd657a4e259a74c7dbfaa48b00
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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