Potassium Cyanide → 2-(2-Chloro-6-methylphenyl)acetonitrile

HRID 1679896Notes

Reaction equation

HRID 1679896 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[C-:11]#[N:12].[K+]>C(O)C.O>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[CH2:2][C:11]#[N:12]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 200723601-Chloro-2-(chloromethyl)-3-methylbenzene

Product 1

HCID 542461202-(2-Chloro-6-methylphenyl)acetonitrileYield 55.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 9.4 g of alpha,2-dichloro-6-methyltoluene in 30 ml of 95% ethanol is treated with a solution of 3.8 g of potassium cyanide in 5 ml of water and heated at reflux for 6 hours. The crude product is isolated by pouring the cooled reaction mixture into water and filtering the precipitated solid. Recrystallization from aqueous ethanol gives 4.9 g of pure 2-chloro-6-methylphenylacetonitrile, mp 49°-51° C., in two crops.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customThe crude product is isolated
  4. additionby pouring
  5. filtrationfiltering the precipitated solid
  6. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-c10ee08f24c64aebae511d75d13b753c
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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