Reaktion #1448

Reaktionsgleichung

benzyl cyanide

1,4-dibromobutane

water

ethyl acetate

→

1-phenylcyclopentanecarboxylic acid

Lösungsmittel

sodium hydride

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGagain stirred for 16 hours at room temperature
2. 2
   Sonstigethe resulting organic layer was separated
3. 3
   Waschenwashed with a saturated sodium chloride aqueous solution
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeAfter removing the solvent
6. 6
   workup.DISTILLATIONby distillation under a reduced pressure
7. 7
   workup.ADDITIONthe resulting hexane eluate was mixed with 45 ml of sulfuric acid
8. 8
   workup.WAITsubjected to 24 hours
9. 9
   Temperaturof heating
10. 10
    Temperaturunder reflux
11. 11
    TemperaturAfter cooling down to room temperature
12. 12
    workup.ADDITIONthe reaction solution was mixed with ice water and ethyl acetate
13. 13
    Sonstigeto separate water layer which
14. 14
    workup.ADDITIONwas subsequently mixed with concentrated hydrochloric acid and ethyl acetate
15. 15
    Sonstigethe resulting organic layer was separated
16. 16
    Waschenwashed with water
17. 17
    Trocknena saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
18. 18
    SonstigeBy removing the solvent
19. 19
    workup.DISTILLATIONby distillation under a reduced pressure

Vorschrift

In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with water and ethyl acetate, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography, and the resulting hexane eluate was mixed with 45 ml of sulfuric acid and subjected to 24 hours of heating under reflux. After cooling down to room temperature, the reaction solution was mixed with ice water and ethyl acetate to separate water layer which was subsequently mixed with concentrated hydrochloric acid and ethyl acetate, and the resulting organic layer was separated, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. By removing the solvent by distillation under a reduced pressure, 978 mg of 1-phenylcyclopentanecarboxylic acid was obtained.

Quelle