Potassium Cyanide → 4-Chloro-2-methylbenzeneacetonitrile

HRID 1806785Notes

Reaction equation

HRID 1806785 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[C:4]([CH3:10])[CH:3]=1.[C-:11]#[N:12].[K+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 128226184-Chloro-1-(chloromethyl)-2-methylbenzene

Product 1

HCID 184099344-Chloro-2-methylbenzeneacetonitrileYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Step B To a solution of 4-chloro-2-methylbenzyl chloride (5.2 g, 30 mmol) in ethanol (40 mL) was added an aqueous solution (30 mL) of KCN (5 g, 77 mmol) at room temperature. The reaction mixture was then heated at 100° C. for 2 h. The mixture was cooled to room temperature and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:10, then 1:4) to give 4-chloro-2-methylbenzyl cyanide as a yellow oil (3.5 g, 66%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-af47db2144e14e4083848c84f1b7a058
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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