Reacción #54871

Ecuación de reacción

4-chlorobutyronitrile

amyl bromide

magnesium

ether

hydrochloric acid

→

1-Chloro-4-nonanone

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente