Réaction #2307972

Équation de réaction

Benzyl chloride

sodium hydroxide

NaOH

hexaethylene glycol

→

monodispersed compound 1

Rendement 70.6%

Hexaethylene glycol monobenzyl ether

Rendement 70.6%

Solvants

brine

water

Conditions de réaction

Traitement

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

Mode opératoire

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