Phenol → Diglycidyl ether

HRID 1608456Notes

Reaction equation

HRID 1608456 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+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C)C=O>[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

The starting phenol derivative (2.50 g) of the following formula: ##STR25## and R-(-)-epichlorohydrin (chemical purity: 98.5% or more, optical purity: 99% or more, 4.25 g) and benzyltriethylammonium chloride (20 mg) are dissolved in dimethylformamide (3 ml) and thereto is added dropwise 24 wt. % aqueous sodium hydroxide (1.2 equivalent) at 60° C. After reacting at the same temperature for 40 minutes, the reaction mixture is cooled to room temperature and extracted with ether. The extract is distilled under reduced pressure to remove the solvent. The residue is purified by silica gel chromatography to give S isomer of glycidyl ether (1.62 g) of the following formula: ##STR26##

Workup

  1. extractionextracted with ether
  2. distillationThe extract is distilled under reduced pressure
  3. customto remove the solvent
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-d418147ce14d4709882bb9321dda59ed
Source dataset
uspto-grants-1995_03
Patent number
US05395553

Reaction notes

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