Ethylene Glycol → 2-[2-[2-(2-Chloroethoxy)ethoxy]ethoxy]ethanol

HRID 1938138

Reaction equation

HRID 1938138 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][Cl:10].[OH-].[K+].[CH2:13]([OH:16])[CH2:14][OH:15]>>[Cl:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:15][CH2:14][CH2:13][OH:16]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 81711,2-Bis(2-chloroethoxy)ethaneHCID 14797Potassium Hydroxide

Product 1

HCID 1384342-[2-[2-(2-Chloroethoxy)ethoxy]ethoxy]ethanolYield 30%

Procedure

A solution of 1,8-dichloro-3, 6-dioxaoctane (40 g) and potassium hydroxide (11.8 g) in ethylene glycol (100 ml) was stirred at 100° C. for 18 h. The mixture was then cooled, filtered and the residue washed with acetone (2×35 ml). The combined filtrate was then distilled to yield the product as a clear oil (13.5 g, 30%), b.p. 120°-122° C. /0.2 mm Hg; I.r. (liquid film) 3430 cm-1.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. washthe residue washed with acetone (2×35 ml)
  4. distillationThe combined filtrate was then distilled

Sources & evidence

ORD record
ord-04ebba5ff6234909ac777d2d5fcef81d
Source dataset
uspto-grants-1997_12
Patent number
US05693477

Linked notes

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