Sodium Cyanide → 3,3-Dicyclopropylpropionitrile

HRID 1975310Notes

Reaction equation

HRID 1975310 reaction equation
S(O[CH2:12][CH:13]([CH:17]1[CH2:19][CH2:18]1)[CH:14]1[CH2:16][CH2:15]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:20]#[N:21].[Na+]>CS(C)=O>[CH:17]1([CH:13]([CH:14]2[CH2:15][CH2:16]2)[CH2:12][C:20]#[N:21])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 542793502,2-Dicyclopropylethanol tosylate

Product 1

HCID 107730223,3-DicyclopropylpropionitrileYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
95 °C

Procedure

209 g of 2,2-dicyclopropylethanol tosylate (prepared from 2,2-dicyclopropylethanol and para-toluenesulfonyl chloride) in solution in 45 ml of DMSO, are slowly added to 40 g of sodium cyanide in 45 ml of dimethyl sulfoxide (DMSO), with stirring and at 95° C. The heating is continued for one hour. After filtration of the precipitate and washing with ethyl ether, the filtrates are pooled, washed with a saturated solution of sodium chloride, dried and evaporated. The expected product is obtained after distillation under vacuum.

Workup

  1. filtrationAfter filtration of the precipitate
  2. washwashing with ethyl ether
  3. washwashed with a saturated solution of sodium chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e9c1c1d99eb644febf964aa437653ca3
Source dataset
uspto-grants-1994_02
Patent number
US05286732

Reaction notes

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