Reaction #54871

Reaction equation

4-chlorobutyronitrile

amyl bromide

magnesium

ether

hydrochloric acid

→

1-Chloro-4-nonanone

Conditions

Workup

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

Procedure

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).

Source