Phenol → Diglycidyl ether

HRID 1165406Notes

Reaction equation

HRID 1165406 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: ##STR29## the same R-(-)-epichlorohydrin (2.01 g) as used in Preparation 2 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 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 glycidyl ether (380 mg) of the following formula: ##STR30##

Workup

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

Sources & evidence

ORD record
ord-dcc02f7b756347e0b87e841bc0e0bc11
Source dataset
uspto-grants-1990_03
Patent number
US04909957

Reaction notes

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