Ethanol → 5-Decynenitrile, 9-oxo-

HRID 371782Notes

Reaction equation

HRID 371782 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+].[OH-].[Na+]>O.CCOCC>[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 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 114352145-Nonyn-2-one, 9-chloro-

Product 1

HCID 114009605-Decynenitrile, 9-oxo-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

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° C. for about 24 hours, then is cooled and diluted with ether, and then 20 parts by volume of dilute aqueous sodium hydroxide is added with stirring. The layers are separated and the alkaline layer is extracted with ether. The ether extracts are combined, 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 adsorption maximum at 2250 reciprocal centimeters and nuclear magnetic resonance peaks at δ2.15 and δ2.50.

Workup

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

Sources & evidence

ORD record
ord-b66a8562efc74edaae802b71612ecafb
Source dataset
uspto-grants-1978_05
Patent number
US04087621

Reaction notes

Loading…