Phenol → Diglycidyl ether

HRID 1074118Notes

Reaction equation

HRID 1074118 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: ##STR41## the same R-(-)-epichlorohydrin (16.07 g) as used in Preparation 3, 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 dichloromethane to obtain a crude product (11.67 g). The crude product is purified by silica gel column chromatography to give S isomer of a glycidyl ether (9.07 g) of the following formula: ##STR42##

Workup

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

Sources & evidence

ORD record
ord-dd09dc589f134d04adb8eeaa228075ea
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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