Potassium Cyanide → 2-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

HRID 1019506Notes

Reaction equation

HRID 1019506 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][CH:6]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7]1>CS(C)=O.O>[C:1]([CH2:5][CH:6]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7]1)#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 983332-Bromomethyl-1,4-benzodioxane

Product 1

HCID 2675312-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Potassium cyanide (2.05 g, 31.5 mmol) was added to 2-bromomethyl-(2,3 dihydrobenzo[1,4]dioxine) (6.87 g, 30 mmol) in DMSO (90 mL) and stirred at ambient temperature for 20 h. The reaction mixture was then diluted with water (250 mL) and extracted twice with diethyl ether. The diethyl ether was washed with water, then washed twice with brine, dried (Na2SO4) and evaporated in vacuo to yield 2-cyanomethyl-(2,3 dihydrobenzo[1,4]dioxine) as a white solid.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe diethyl ether was washed with water
  3. washwashed twice with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-94e7b913f130437dae1243f79fb2bbc5
Source dataset
uspto-grants-2014_05
Patent number
US08716231B2

Reaction notes

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