Phenol → Diglycidyl ether

HRID 1586611Notes

Reaction equation

HRID 1586611 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5]C=CC=1.[CH2:8]1[O:10][C@H:9]1[CH2:11]Cl.[OH-:13].[Na+]>CN(C)C=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:11]([O:7][CH2:1][CH:6]1[O:13][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

6

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

In 3 ml of dimethylformamide were dissolved 2.50 g of a phenol derivative represented by the formula ##STR15## 4.25 g of R-(-)-epichlorohydrin and 20 mg of benzyltriethyl ammonium chloride, and 1.2 equivalents of 24 wt. % aqueous solution of sodium hydroxide was added dropwise to the solution at 60° C. The mixture was reacted at the same temperature for 40 minutes, the reaction mixture was then cooled to room temperature and subjected to extraction with ether, and the extract was distilled in a vacuum to remove the solvent. The residue was purified by silica gel column chromatography, giving 1.62 g of glycidyl ether of S-configuration having the following characteristics values.

Workup

  1. additionwas added dropwise to the solution at 60° C
  2. customThe mixture was reacted at the same temperature for 40 minutes
  3. extractionsubjected to extraction with ether
  4. distillationthe extract was distilled in a vacuum
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-33008f15a38b4deb985ad76d37f21637
Source dataset
uspto-grants-1993_06
Patent number
US05215678

Reaction notes

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