Reacción #1519084

Ecuación de reacción

Benzyl chloride

sodium hydroxide

NaOH

hexaethylene glycol

→

monodispersed compound 1

Rendimiento 70.6%

Hexaethylene glycol monobenzyl ether

Rendimiento 70.6%

Disolventes

brine

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   TemperaturaThe reaction mixture was then cooled
3. 3
   Extracciónextracted with methylene chloride (200 ml×2)
4. 4
   LavadoThe combined organic layers were washed with brine once
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo to a dark brown oil
8. 8
   OtroThe crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol)

Procedimiento

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.

Fuente