Ethanol → 2,4,6-Trimethylphenylacetonitrile

HRID 966098Notes

Reaction equation

HRID 966098 reaction equation
[C-:1]#[N:2].[Na+].C(O)C.Cl[CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17]>O>[CH3:17][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[C:14]([CH3:15])[C:9]=1[CH2:8][C:1]#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 741082,4,6-Trimethylbenzyl chloride

Product 1

HCID 5206982,4,6-Trimethylphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

66 g of sodium cyanide is refluxed in 100 mL water and 140 mL of ethanol with stirring, until a clear solution is formed. 136 g of 2-chloromethyl-1,3,5-trimethylbenzene is slowly added dropwise to this solution and the mixture is refluxed for 3 hours with stirring. It is diluted with 1 L of water and extracted three times with 200 mL of benzene. The combined organic phases are washed with water and the solvent is distilled off under reduced pressure. The residue is fractionally distilled. Yield: 92 g (72%); bp15: 145° C.-153° C.

Workup

  1. customis formed
  2. temperaturethe mixture is refluxed for 3 hours
  3. extractionextracted three times with 200 mL of benzene
  4. washThe combined organic phases are washed with water
  5. distillationthe solvent is distilled off under reduced pressure
  6. distillationThe residue is fractionally distilled
  7. custom145° C.-153° C.

Sources & evidence

ORD record
ord-cd23e00fb2fd4e78b8755a09f85ebe32
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

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