Phenol → Diglycidyl ether

HRID 1165403Notes

Reaction equation

HRID 1165403 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5]C=CC=1.[CH3:8][C:9](C)([O-:11])[CH3:10].[K+].C([OH:18])(C)(C)C>>[CH2:8]([O:7][CH2:1][CH:6]1[O:18][CH2:5]1)[CH:9]1[O:11][CH2:10]1

Participants

4

Reactant 3

HCID 996PhenolHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 16704Diglycidyl ether

Conditions

Temperature
60 °C

Procedure

A phenol derivative (5.28 g) of the following formula: ##STR21## S-(+)-epichlorohydrin (11.55 g), potassium t-butoxide (3.00 g) and t-butyl alcohol (45 ml) are mixed, the mixture is stirred at 60° C. for 3 hours. The reaction mixture is distilled under reduced pressure to remove the solvent and the residue is extracted with chloroform. The extract is distilled under reduced pressure to remove the solvent. The residue is purified by silica gel chromatography to give R isomer of glycidyl ether(5.82 g) of the following formula: ##STR22##

Workup

  1. distillationThe reaction mixture is distilled under reduced pressure
  2. customto remove the solvent
  3. extractionthe residue is extracted with chloroform
  4. distillationThe extract is distilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e99bedf07ec4639836f7d3f4cfa0174
Source dataset
uspto-grants-1990_03
Patent number
US04909957

Reaction notes

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