反応 #75238

反応方程式

4-chlorobutyronitrile

amyl bromide

magnesium

ether

hydrochloric acid

→

1-Chloro-4-nonanone

反応条件

後処理

1. 1
   workup.ADDITIONis added
2. 2
   workup.WAITis continued for an additional one hour
3. 3
   その他The ether layer is separated quickly
4. 4
   温度The aqueous layer is heated on a steam bath for one hour
5. 5
   その他the separation of the ketone as an oil
6. 6
   温度After cooling
7. 7
   抽出the oil is extracted with ether
8. 8
   洗浄the combined extracts are washed with saturated sodium chloride solution
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    その他The solvent is removed under vacuum
11. 11
    workup.DISTILLATIONthe residual oil is distilled
12. 12
    その他to give 69.0 g

実験手順

To the Grignard reagent prepared from a mixture of amyl bromide (226.59 g.; 1.5 moles) and magnesium (36.48 g.; 1.5 moles) in ether (1000 ml.) is added, dropwise, during one hour, 4-chlorobutyronitrile (155.34 g.; 1.5 moles). Stirring is continued for an additional one hour. The reaction mixture is poured into a mixture of finely crushed ice (1000 g.) and concentrated hydrochloric acid (750 ml.). The ether layer is separated quickly and discarded. The aqueous layer is heated on a steam bath for one hour to hydrolyze the intermediate imine and cause the separation of the ketone as an oil. After cooling, the oil is extracted with ether and the combined extracts are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the residual oil is distilled to give 69.0 g. (26%) of colorless oil, b.p. 115°-117° C./14 mm.; pmr (CDCl3) δ 0.090 (3H,t), 3.56 (2H,t,CH2Cl).

出典