Phenol → Diglycidyl ether

HRID 1109945Notes

Reaction equation

HRID 1109945 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-].[Na+].CN(C)C=[O:18]>O>[CH2:11]([O:7][CH2:1][CH:6]1[O:18][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the starting phenol derivative (10 g) of the following formula: ##STR25## the same R-(-)-epichlorohydrin (16.07 g) as used in Preparation 2, 20 wt. % aqueous sodium hydroxide (7.33 g) and dimethylformamide (20 ml) is heated with stirring at 60°-70° C. for one hour. The reaction mixture is cooled and thereto is added water. The mixture is extracted with chloroform to obtain a crude product (11.67 g). The crude product is purified by silica gel chromatography to give S isomer of glycidyl ether (9.07 g) of the following formula: ##STR26##

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. extractionThe mixture is extracted with chloroform
  4. customto obtain a crude product (11.67 g)
  5. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-2b21f16f86184cb88a09cc915de6a51d
Source dataset
uspto-grants-1994_06
Patent number
US05324450

Reaction notes

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