Phenol → Diglycidyl ether

HRID 1720842Notes

Reaction equation

HRID 1720842 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

5.28 g of a phenol derivative represented by the following formula: ##STR19## 11.55 g of S-(+)-epichlorohydrin (chemical purity: 98.5% or more, optical purity: 99% or more), 3.00 g of potassium tert-butoxide and 45 ml of tert-butyl alcohol were mixed and stirred for 3 hours at 60° C. After evaporating the solvent from the reaction mixture at reduced pressure, the resultant was subjected to extraction with chloroform followed by evaporation of the solvent. The residue was purified by a silica gel column chromatography to obtain 5.82 g of a R-isomer of glycidyl ether represented by the following formula (Intermediate 2). ##STR20##

Workup

  1. customAfter evaporating the solvent from the reaction mixture at reduced pressure
  2. extractionthe resultant was subjected to extraction with chloroform
  3. customfollowed by evaporation of the solvent
  4. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-bd2d605b7e4a42cbb2cce7ffa94eac09
Source dataset
uspto-grants-1996_04
Patent number
US05507975

Reaction notes

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