Ethanol → 5-Decynenitrile, 9-oxo-

HRID 27793Notes

Reaction equation

HRID 27793 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10].C(O)C.[C-:15]#[N:16].[Na+]>O.CCOCC.[OH-].[Na+]>[C:15]([CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])#[N:16]

Participants

7

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 114352145-Nonyn-2-one, 9-chloro-

Product 1

HCID 114009605-Decynenitrile, 9-oxo-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution consisting of 2.77 parts of 9-chloro-5-nonyn-2-one in 8 parts by volume of ethanol is added a solution containing 2.77 parts of sodium cyanide dissolved in 4 parts of water. The resulting reaction mixture is heated at 80°-100° for about 24 hours, then is cooled and diluted with ether, whereupon 20 parts by volume of dilute aqueous sodium hydroxide is added with stirring. The layers are separated and the alkaline layer extracted with ether. The ether extracts are combined, then washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 9-cyano-5-nonyn-2-one. This compound exhibits an infrared absorption maximum at 2250 reciprocal centimeters and nuclear magnetic resonance peaks at δ2.18 and δ2.50.

Workup

  1. additionis added a solution
  2. customThe resulting reaction mixture
  3. temperatureis heated at 80°-100° for about 24 hours
  4. temperatureis cooled
  5. additionis added
  6. customThe layers are separated
  7. extractionthe alkaline layer extracted with ether
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-697c42f56e994d0894e9a7f91ba0a0c9
Source dataset
uspto-grants-1980_09
Patent number
US04223158

Reaction notes

Loading…