Epichlorohydrin → 1,2-Epoxy-3-[2-(2-hydroxyethoxy)phenoxy]propane

HRID 1979750Notes

Reaction equation

HRID 1979750 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]1[O:7][CH2:6]1)Cl.[OH:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[O:11][CH2:12][CH2:13][OH:14]>O1CCOCC1>[O:7]1[CH:5]([CH2:3][O:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[O:11][CH2:12][CH2:13][OH:14])[CH2:6]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 785192-(2-Hydroxyethoxy)phenol

Product 1

HCID 131032411,2-Epoxy-3-[2-(2-hydroxyethoxy)phenoxy]propaneYield 41.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

69 ml of 1N sodium hydroxide and 7.3 ml of epichlorohydrin were added to a solution of 7.2 g of 2-(2-hydroxyphenoxy)ethanol in 50 ml of dioxane, and the mixture was heated at 50° C. for 2 hours with stirring. The reaction solution was extracted with chloroform, washed with water and dried. The solvent was distilled off under reduced pressure. The residue was chromatographed on a silica gel column to afford 4.1 g (yield 41.7%) of 1,2-epoxy-3-[2-(2-hydroxyethoxy)phenoxy]propane as a colorless oil.

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. washwashed with water
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-410815a1a836463d970efe5b9e13429d
Source dataset
uspto-grants-1984_11
Patent number
US04482562

Reaction notes

Loading…