반응 #1519084

반응 방정식

Benzyl chloride

sodium hydroxide

NaOH

hexaethylene glycol

→

monodispersed compound 1

수율 70.6%

Hexaethylene glycol monobenzyl ether

수율 70.6%

용매

brine

water

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도The reaction mixture was then cooled
3. 3
   추출extracted with methylene chloride (200 ml×2)
4. 4
   세척The combined organic layers were washed with brine once
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo to a dark brown oil
8. 8
   기타The crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol)

실험 절차

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.

출처