Diethylene Glycol → Pentaethylene glycol monomethyl ether

HRID 1379006Notes

Reaction equation

HRID 1379006 reaction equation
[Na].[CH2:2]([OH:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].[CH2:9](Cl)[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18]>C(Cl)Cl>[CH2:2]([OH:8])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 5478521-Chloro-3,6,9-trioxadecaneHCID 5360545Sodium

Product 1

HCID 90255Pentaethylene glycol monomethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Under argon, 630 mg (27.4 mmol) of sodium are added to 10 ml of diethylene glycol and the mixture is heated for one hour at 100° C. At that temperature, 5 g (27.4 mmol) of 3,6,9-trioxadecyl chloride are added dropwise thereto using a syringe. The mixture is stirred overnight at 100° C. to complete the reaction. After cooling, the reaction solution is taken up in CH2Cl2, washed with water and brine and dried over Na2SO4. Removal of the solvent yields 3,6,9,12,15-pentaoxa-hexadecanol in the form of an oil (Liebigs Ann. Chem. 1980, 858); NMR(CDCl3): 3.8-3.5 (m,20H); 3.75 (s,3H).

Workup

  1. customthe reaction
  2. temperatureAfter cooling
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-83fa64ecdb36492d8f9354327f7e3f3c
Source dataset
uspto-grants-1997_09
Patent number
US05670491

Reaction notes

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