Phenol → Diglycidyl ether

HRID 1074119Notes

Reaction equation

HRID 1074119 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 (7.44 g) of the following formula: ##STR43## as prepared in Preparation 1, the same R-(-)-epichlorohydrin (9.16 g) as used in Preparation 3, 50 wt. % aqueous sodium hydroxide (1.74 g) and dimethylformamide (77 ml) is stirred at 60°-70° C. for 3 hours. The reaction mixture is cooled and thereto is added water, and the mixture is extracted with dichloromethane. The extracted product is purified by silica gel column chromatography to give S isomer of a glycidyl ether (6.90 g) of the following formula: ##STR44##

Workup

  1. custom##STR43## as prepared in Preparation 1
  2. temperatureThe reaction mixture is cooled
  3. extractionthe mixture is extracted with dichloromethane
  4. customThe extracted product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-886cc334ea0a49048d421b687a9fd950
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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