Réaction #1448

Équation de réaction

benzyl cyanide

1,4-dibromobutane

water

ethyl acetate

→

1-phenylcyclopentanecarboxylic acid

Solvants

sodium hydride

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGagain stirred for 16 hours at room temperature
2. 2
   Autrethe resulting organic layer was separated
3. 3
   Lavagewashed with a saturated sodium chloride aqueous solution
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   AutreAfter 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
   Températureof heating
10. 10
    Températureunder reflux
11. 11
    TempératureAfter cooling down to room temperature
12. 12
    workup.ADDITIONthe reaction solution was mixed with ice water and ethyl acetate
13. 13
    Autreto separate water layer which
14. 14
    workup.ADDITIONwas subsequently mixed with concentrated hydrochloric acid and ethyl acetate
15. 15
    Autrethe resulting organic layer was separated
16. 16
    Lavagewashed with water
17. 17
    Séchagea saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
18. 18
    AutreBy removing the solvent
19. 19
    workup.DISTILLATIONby distillation under a reduced pressure

Mode opératoire

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.

Source