Acetonitrile → 3-Cyclohexyl-3-oxopropanenitrile

HRID 727277Notes

Reaction equation

HRID 727277 reaction equation
[H-].[Na+].[C:3](#[N:5])[CH3:4].[CH:6]1([C:12](OC)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C1C=CC=CC=1>[CH:6]1([C:12]([CH2:4][C:3]#[N:5])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 20748Methyl cyclohexanecarboxylateHCID 24758Sodium hydride

Product 1

HCID 113095973-Cyclohexyl-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

60% Sodium hydride (oil suspension) is added to benzene (90 ml) and the mixture is refluxed under heating. Acetonitrile (23 ml) dissolved in benzene (23 ml) is added and the mixture is refluxed for 1 hour. A solution of methyl cyclohexanecarboxylate (63 g) dissolved in benzene (70 ml) is dropwise added and the mixture is refluxed under heating for 5 hours. After the completion of the reaction, the mixture is cooled to room temperature and poured into ice water (200 ml). The organic layer is removed and the aqueous layer is washed with isopropyl ether. The aqueous layer is adjusted to pH 2 with conc. hydrochloric acid and extracted 3 times with isopropyl ether. The extract is dried over anhydrous magnesium sulfate and the solvent is distilled away under reduced pressure to give 34 g of cyanomethyl cyclohexyl ketone. The obtained cyanomethyl cyclohexyl ketone (34 g), morpholine (17.6 ml) and ethyl methyl ketone (18 ml) are dissolved in ethanol (150 ml) and sulfur (6.47 g) is suspended. The suspension is refluxed under heating for 10 hours. After the completion of the reaction, the solvent is distilled away under reduced pressure.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating
  3. additionis added
  4. temperaturethe mixture is refluxed for 1 hour
  5. additionis dropwise added
  6. temperaturethe mixture is refluxed
  7. temperatureunder heating for 5 hours
  8. customAfter the completion of the reaction
  9. customThe organic layer is removed
  10. washthe aqueous layer is washed with isopropyl ether
  11. extractionextracted 3 times with isopropyl ether
  12. dry with materialThe extract is dried over anhydrous magnesium sulfate
  13. distillationthe solvent is distilled away under reduced pressure

Sources & evidence

ORD record
ord-3369003ad61f418c8edfd7eee37e3127
Source dataset
uspto-grants-1998_01
Patent number
US05712274

Reaction notes

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