Reaction #1519084

Reaction equation

Benzyl chloride

sodium hydroxide

NaOH

hexaethylene glycol

→

monodispersed compound 1

Yield 70.6%

Hexaethylene glycol monobenzyl ether

Yield 70.6%

Solvents

brine

water

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was heated
2. 2
   TemperatureThe reaction mixture was then cooled
3. 3
   Extractionextracted with methylene chloride (200 ml×2)
4. 4
   WashThe combined organic layers were washed with brine once
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo to a dark brown oil
8. 8
   OtherThe crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol)

Procedure

An aqueous sodium hydroxide solution prepared by dissolving 3.99 g (100 mmol) NaOH in 4 ml water was added slowly to monodispersed hexaethylene glycol (28.175 g, 25 ml, 100 mmol). Benzyl chloride (3.9 g, 30.8 mmol, 3.54 ml) was added and the reaction mixture was heated with stirring to 100° C. for 18 hours. The reaction mixture was then cooled, diluted with brine (250 ml) and extracted with methylene chloride (200 ml×2). The combined organic layers were washed with brine once, dried over Na2SO4, filtered and concentrated in vacuo to a dark brown oil. The crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol) to yield 8.099 g (70%) of monodispersed compound 1 as a yellow oil.

Source