Water → 1-Phenylcyclopentanecarboxylic acid

HRID 1352

Reaction equation

HRID 1352 reaction equation
C(C#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.O.[C:17]([O:20]CC)(=[O:19])[CH3:18]>[H-].[Na+].O1CCCC1>[C:2]1([C:18]2([C:17]([OH:20])=[O:19])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 8857Ethyl Acetate

Product 1

HCID 661671-Phenylcyclopentanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d699a2fd0bfb49f2b2d9d51a6a3e6ab2
Source dataset
uspto-grants-1998_03
Patent number
US05723606

Linked notes

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