反应详情

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.

1. stirringagain stirred for 16 hours at room temperature
2. customthe resulting organic layer was separated
3. washwashed with a saturated sodium chloride aqueous solution
4. dry with materialdried over anhydrous magnesium sulfate
5. customAfter removing the solvent
6. distillationby distillation under a reduced pressure
7. additionthe resulting hexane eluate was mixed with 45 ml of sulfuric acid
8. waitsubjected to 24 hours
9. temperatureof heating
10. temperatureunder reflux
11. temperatureAfter cooling down to room temperature
12. additionthe reaction solution was mixed with ice water and ethyl acetate
13. customto separate water layer which
14. additionwas subsequently mixed with concentrated hydrochloric acid and ethyl acetate
15. customthe resulting organic layer was separated
16. washwashed with water
17. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
18. customBy removing the solvent
19. distillationby distillation under a reduced pressure