تفاعل #75238

معادلة التفاعل

4-chlorobutyronitrile

amyl bromide

magnesium

ether

hydrochloric acid

→

1-Chloro-4-nonanone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added
2. 2
   workup.WAITis continued for an additional one hour
3. 3
   أخرىThe ether layer is separated quickly
4. 4
   درجة الحرارةThe aqueous layer is heated on a steam bath for one hour
5. 5
   أخرىthe separation of the ketone as an oil
6. 6
   درجة الحرارةAfter cooling
7. 7
   استخلاصthe oil is extracted with ether
8. 8
   غسيلthe combined extracts are washed with saturated sodium chloride solution
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    أخرىThe solvent is removed under vacuum
11. 11
    workup.DISTILLATIONthe residual oil is distilled
12. 12
    أخرىto give 69.0 g

الإجراء التجريبي

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).

المصدر