Phenol → Diglycidyl ether

HRID 1074116Notes

Reaction equation

HRID 1074116 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.CC(C)([O-:16])C.[K+]>C(O)(C)(C)C>[CH2:11]([O:7][CH2:1][CH:6]1[O:16][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

5

Reactant 3

HCID 996PhenolHCID 2734062(-)-EpichlorohydrinHCID 23665647Potassium tert-butoxide

Product 1

HCID 16704Diglycidyl etherYield 139.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

The starting phenol derivative (13 g) of the following formula: ##STR35## and the same R-(-)-epichlorohydrin (13.2 g) as used in Preparation 3, potassium t-butoxide (8.8 g) and t-butyl alcohol (80 ml) are mixed and stirred at 60° C. for 2 hours. After the reaction mixture is concentrated, chloroform is added to the concentrate and the resultant is washed with a saturated saline solution and dried over anhydrous magnesium sulfate. Chloroform is distilled away under reduced pressure to give a crude product. The crude product is purified by silica gel column chromatography to give S isomer of a glycidyl ether (14.2 g) of the following formula: ##STR36##

Workup

  1. additionare mixed
  2. concentrationAfter the reaction mixture is concentrated
  3. additionchloroform is added to the
  4. concentrationconcentrate
  5. washthe resultant is washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationChloroform is distilled away under reduced pressure
  8. customto give a crude product
  9. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54d2b772ee65465bb8942453c4d05cab
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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