Реакция #1519084

Уравнение реакции

Benzyl chloride

sodium hydroxide

NaOH

hexaethylene glycol

→

monodispersed compound 1

Выход 70.6%

Hexaethylene glycol monobenzyl ether

Выход 70.6%

Растворители

brine

water

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   ТемператураThe reaction mixture was then cooled
3. 3
   Экстракцияextracted with methylene chloride (200 ml×2)
4. 4
   ПромывкаThe combined organic layers were washed with brine once
5. 5
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated in vacuo to a dark brown oil
8. 8
   ДругоеThe crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol)

Методика

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.

Источник