Phenol → Diglycidyl ether

HRID 1165407Notes

Reaction equation

HRID 1165407 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>[CH2:11]([O:7][CH2:1][CH:6]1[O:13][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

5

Reactant 3

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

Product 1

HCID 16704Diglycidyl etherYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the starting phenol derivative (3.12 g) of the following formula: ##STR31## the same R-(-)-epichlorohydrin (4.627 g) as used in Preparation 2, 50 wt. % aqueous sodium hydroxide (0.88 g) and dimethylformamide (30 ml) is heated with stirring at 60° C. for 2.5 hours. The reaction mixture is cooled and distilled under reduced pressure to remove the solvent. The product is purified by silica gel chromatography to give S isomer of glycidyl ether (2.96 g) of the following formula: ##STR32##

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-71b3c69df7a443ed804c6a414a348ca8
Source dataset
uspto-grants-1990_03
Patent number
US04909957

Reaction notes

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