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

HRID 1758718Notes

Reaction equation

HRID 1758718 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 1 N 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-7a91faad5f03423ba7e0d2b50f00f379
Source dataset
uspto-grants-1983_02
Patent number
US04374840

Reaction notes

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