Phenol → Diglycidyl ether

HRID 1074121Notes

Reaction equation

HRID 1074121 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: ##STR47## the same R-(-)-epichlorohydrin (4.627 g) as used in Preparation 3, 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 column chromatography to give S isomer of a glycidyl ether (2.96 g) of the following formula: ##STR48##

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 column chromatography

Sources & evidence

ORD record
ord-2c36da7dc94d4666960beb805ad05f77
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

Loading…