Phenol → Diglycidyl ether

HRID 1074120Notes

Reaction equation

HRID 1074120 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+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[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 27.2%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
70 °C

Procedure

The starting phenol derivative (1.01 g) of the following formula: ##STR45## the same R-(-)-epichlorohydrin (2.01 g) as used in Preparation 3 and benzyltriethylammonium chloride (16 mg) are mixed and heated at 70° C., and thereto is added dropwise 24 wt. % aqueous sodium hydroxide (650 mg). The mixture is stirred at 70° C. for 2 hours. The reaction mixture is left to stand to be cooled to room temperature and extracted three times with chloroform. The extract is dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue is recrystallized from hexane to give S isomer of a glycidyl ether (380 mg) of the following formula: ##STR46##

Workup

  1. additionare mixed
  2. waitThe reaction mixture is left
  3. temperatureto be cooled to room temperature
  4. extractionextracted three times with chloroform
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-8ebc0a508f434fea8600bee7ddd28e50
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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