Potassium Cyanide → 3-(Cyanomethyl)-5-methylbenzonitrile

HRID 1804691Notes

Reaction equation

HRID 1804691 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:6]#[N:7].[C-:12]#[N:13].[K+]>C(O)C>[C:12]([CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:6]#[N:7])#[N:13]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 145678603-(Bromomethyl)-5-methylbenzonitrile

Product 1

HCID 667054463-(Cyanomethyl)-5-methylbenzonitrileYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred ethanol (150 mL), was added 3-(bromomethyl)-5-methylbenzonitrile (48 g, 0.228 M), potassium cyanide (27 g, 0.42 M), and distilled water (77 mL). The mixture was then refluxed for 3 hr. After cooling to room temperature, the reaction mixture was evaporated in vacuo and the residue was partitioned between ether and water. The ether layer was taken, dried with anhydrous magnesium sulfate, filtered, evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1)) to afford 18.3 g (51%) of 3-(cyanomethyl)-5-methylbenzonitrile as a pale yellow solid. m.p. 63-64° C. 1H NMR (300 MHz, CDCl3) δ 2.42 (3H, s), 3.77 (2H, s), 7.42 (2H, s), 7.45 (1H, s).

Workup

  1. distillationdistilled water (77 mL)
  2. temperatureThe mixture was then refluxed for 3 hr
  3. customthe reaction mixture was evaporated in vacuo
  4. customthe residue was partitioned between ether and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1))

Sources & evidence

ORD record
ord-2f8355b96f9f445c88cd5154e9021302
Source dataset
uspto-grants-2013_01
Patent number
US08354421B2

Reaction notes

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