Phenol → Diglycidyl ether

HRID 1492349Notes

Reaction equation

HRID 1492349 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.CN(C)C=O>[CH2:11]([O:7][CH2:1][CH:6]1[O:13][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

6

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

2.50 g of a phenol derivative of the formula: ##STR36## 4.25 g of R-(-)-epichlorohydrin and 20 mg of benzyl triethyl ammonium chloride (the latter two compounds were the same ones as used in Preparation 1) were dissolved in 3 ml of dimethylformamide. To the solution was dropwise added 24% by weight sodium hydroxide aqueous solution (1.2 equivalents) at 60° C. The mixture was allowed to react for 40 minutes at the same temperature, then cooled to room temperature and extracted with ether. The solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography to obtain an S isomer of glycidyl ether (1.62 g) of the following formula: ##STR37## mp: 90° C. [α]D25 : +4.44° (C=1.01, CH2Cl2)

Workup

  1. customas used in Preparation 1)
  2. customat 60° C
  3. customto react for 40 minutes at the same temperature
  4. extractionextracted with ether
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ece765a8025c4f7585139dc235fcf729
Source dataset
uspto-grants-1994_12
Patent number
US05374373

Reaction notes

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