Sodium Cyanide → 1,3-Dioxolane-2-propiononitrile

HRID 888757Notes

Reaction equation

HRID 888757 reaction equation
[C-:1]#[N:2].[Na+].[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[CH2:9][CH2:10]Br>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[CH2:9][CH2:10][C:1]#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 877762-(2-Bromoethyl)-1,3-dioxolane

Product 1

HCID 780981,3-Dioxolane-2-propiononitrileYield 88%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

58.8 g (1.2 mol) of sodium cyanide and 22.28 g (0.12 mol) of benzyltrimethylammonium chloride are dissolved in 360 ml of water. Thereafter 181.03 g (1.0 mol) of 2-[1,3]-dioxolan-2-yl-1-bromoethane are added dropwise and the reaction mixture is heated at 90° C. After six hours it is cooled, diluted with 400 ml of water and subjected to extraction with ether. Drying over magnesium sulfate and evaporation of the solvent give 111.85 g of 3-[1,3]-dioxolan-2-yl-propionitrile as a reddish oil which is used without further purification in the next stage of the reaction.

Workup

  1. temperatureAfter six hours it is cooled
  2. extractionsubjected to extraction with ether
  3. dry with materialDrying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-d57b059543014db88b7fde9cb53bd516
Source dataset
uspto-grants-2012_08
Patent number
US08252784B2

Reaction notes

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