Phenol → Diglycidyl ether

HRID 1720841Notes

Reaction equation

HRID 1720841 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.C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-:27].[Na+]>CN(C)C=O>[CH2:11]([O:7][CH2:1][CH:6]1[O:27][CH2:5]1)[CH:9]1[O:10][CH2:8]1

Participants

6

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 17208BenzyltriethylammoniumHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.50 g of a phenol derivative represented by the following formula: ##STR17## 4.25 g of R-(-)-epichlorohydrin (chemical purity: 98.5% or more, optical purity: 99% or more) and 20 mg of benzyltriethylammonium chrolide were dissolved in 3 ml of dimethylformamide. To the solution was added dropwise 24% by weight sodium hydroxide aqueous solution (1.2 equivalents) at 60° C. The reaction was conducted for 40 minutes at the same temperature, and then the reaction mixture was cooled to room temperature followed by extraction with ether. After evaporating the solvent at reduced pressure, the residue was purified by a silica gel column chromatography to obtain 1.62 g of a S-isomer of glycidyl ether represented by the following formula (Intermediate 1). ##STR18##

Workup

  1. extractionfollowed by extraction with ether
  2. customAfter evaporating the solvent at reduced pressure
  3. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-3e7305faedbc4d57bc3f67d24988346c
Source dataset
uspto-grants-1996_04
Patent number
US05507975

Reaction notes

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