Diethylene Glycol → Pentaethylene glycol monomethyl ether

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence