Water → 2-Cyano-5-methoxybenzeneacetonitrile

HRID 500340Notes

Reaction equation

HRID 500340 reaction equation
Br[CH2:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[C:13](#[N:15])C.[C-]#N.[K+].O>C(O)C>[C:13]([CH2:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 1266805128970-91-4

Product 1

HCID 594235252-Cyano-5-methoxybenzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Bromomethyl)-4-methoxybenzonitrile (36 g, example 235, step 1) was suspended in 200 ml of ethanol, 200 ml of acetonitrile was added followed by KCN (8.3 g) and 150 ml of water. Mixture was stirred and the colorless solution turned to yellow. The reaction was complete after 4 hours of stirring. The volatiles were removed under vacuum, and the residual solid was redissolved in ethyl acetate (200 ml) and washed with water (100 ml) and brine (100 ml). The organics were then dried over sodium sulfate. Ethyl acetate was removed and the residue was recrystallized from ethyl acetate and dichloride methane to provide 17 g of 2-(cyanomethyl)-4-methoxybenzonitrile.

Workup

  1. stirringof stirring
  2. customThe volatiles were removed under vacuum
  3. dissolutionthe residual solid was redissolved in ethyl acetate (200 ml)
  4. washwashed with water (100 ml) and brine (100 ml)
  5. dry with materialThe organics were then dried over sodium sulfate
  6. customEthyl acetate was removed
  7. customthe residue was recrystallized from ethyl acetate and dichloride methane

Sources & evidence

ORD record
ord-7954d7c1b7084f48809115a2ba5e4db6
Source dataset
uspto-grants-2010_08
Patent number
US07772180B2

Reaction notes

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