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

HRID 660414Notes

Reaction equation

HRID 660414 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-4dac5eddd16d4582b8eeabb16c56f7d4
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

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