반응 #54871

반응 방정식

4-chlorobutyronitrile

amyl bromide

magnesium

ether

hydrochloric acid

→

1-Chloro-4-nonanone

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   workup.WAITis continued for an additional one hour
3. 3
   기타The ether layer is separated quickly
4. 4
   온도The aqueous layer is heated on a steam bath for one hour
5. 5
   기타the separation of the ketone as an oil
6. 6
   온도After cooling
7. 7
   추출the oil is extracted with ether
8. 8
   세척the combined extracts are washed with saturated sodium chloride solution
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    기타The solvent is removed under vacuum
11. 11
    workup.DISTILLATIONthe residual oil is distilled
12. 12
    기타to give 69.0 g

실험 절차

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) δ0.090 (3H,t), 3.56 (2H,t,CH2Cl).

출처