Acetic Acid → 2-n-Hexyl-3-cyanocyclopentanone

HRID 328056Notes

Reaction equation

HRID 328056 reaction equation
[CH2:1]([C:7]1[C:8](=[O:12])[CH2:9][CH2:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)C.C(O)(=O)C.[C-:20]#[N:21].[K+]>O>[CH2:1]([CH:7]1[CH:11]([C:20]#[N:21])[CH2:10][CH2:9][C:8]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 9032Potassium CyanideHCID 667682-Hexyl-2-cyclopenten-1-one

Product 1

HCID 112984832-n-Hexyl-3-cyanocyclopentanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

In a 3-L three necked flask fitted with a mechanical stirrer, a reflux condenser, a dropping funnel and a thermometer, are placed 83 g of 2-n-hexyl-cyclopentenone, 1.75 L 95% ethyl alcohol and 30 g of glacial acetic acid. The mixtures is warmed up with sirring to 35° C and a solution of 65 g of potassium cyanide in 190 ml of water is added over a period of 15 minutes. Stirring is continued for 3 hours, the temperature being maintained at 35° C. The methanol is then distilled off at a reduced pressure the organic layer is separated, and the water phase is extracted with ether. The combined organic layer and ether extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658.

Workup

  1. temperaturethe temperature being maintained at 35° C
  2. distillationThe methanol is then distilled off at a reduced pressure the organic layer
  3. customis separated
  4. extractionthe water phase is extracted with ether
  5. extractionThe combined organic layer and ether extract
  6. washare washed with sodium carbonate solution and water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customThe solvent is removed at atmospheric pressure
  9. distillationthe residue is distilled through a short Vigreux column
  10. custom2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658

Sources & evidence

ORD record
ord-25bd6571689c4adaa27a3b2c1ad04b05
Source dataset
uspto-grants-1977_04
Patent number
US04016109

Reaction notes

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