Hydrochloric Acid → 1-Phenylcyclohexanecarbonitrile

HRID 2169287Notes

Reaction equation

HRID 2169287 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.Cl>CS(C)=O.CS(C)=O.CCOCC.O>[C:3]1([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 81001,5-DibromopentaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 751481-PhenylcyclohexanecarbonitrileYield 65.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 19869614Ether dimethylsulfoxideSolvent

Procedure

To a suspension of NaH (42.7 g, 1067.0 mmol, 60%) in dimethyl sulfoxide (600.0 mL) were added drop-wise a mixture of phenylacetonitrile (50.0 g, 426.8 mmol) and 1,5-dibromopentane (58.1 mL, 426.8 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (200.0 mL) at 0° C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water and a 10% HCl solution were added to the mixture and the mixture was extracted with ethyl acetate. The combined organic layer was then washed with water and brine and dried over sodium sulfate and concentrated under reduced pressure to obtain a crude product. This crude product was then purified by normal silica gel column chromatography (using hexane) to get 1-phenyl-cyclohexanecarbonitrile (249) (52.0 g, 65.76%) as a colorless oil.

Workup

  1. additionwere added drop-wise
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a crude product
  7. customThis crude product was then purified by normal silica gel column chromatography (using hexane)

Sources & evidence

ORD record
ord-60fd92c382fa47ff86af1ae4cef1a4db
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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