Sodium Cyanide → Nonanenitrile, 3-hydroxy-, (3R)-

HRID 355295Notes

Reaction equation

HRID 355295 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C@H:6]([OH:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>CS(C)=O>[OH:13][C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][C:1]#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 12575177HCID 12575177, compound

Product 1

HCID 11298091Nonanenitrile, 3-hydroxy-, (3R)-Yield 86.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under nitrogen atmosphere, 6.2 g (126 mM) of sodium cyanide and 50 ml of dimethyl sulfoxide (DMSO) were placed in two-necked round-bottomed flask and dissolved by heating, followed by stirring. The solution was left standing and a solution of 10.4 g of (R)-1-chloro2-octanol in 20 ml of DMSO was added dropwise to the solution at 50° C., followed by stirring for 20 hours at 50° C. After the reaction, distilled water was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with distilled water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent under reduced pressure to obtain 8.48 g (54.7 mM) of (R)-3-hydroxynonanenitrile.

Workup

  1. dissolutiondissolved
  2. temperatureby heating
  3. waitThe solution was left
  4. stirringby stirring for 20 hours at 50° C
  5. customAfter the reaction
  6. distillationdistilled water
  7. additionwas added to the reaction mixture
  8. extractionfollowed by extraction with diethyl ether
  9. washThe organic layer was washed with distilled water
  10. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-414bf636e9a147d491a5e1acc25b937b
Source dataset
uspto-grants-1998_11
Patent number
US05830386

Reaction notes

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