Sodium Cyanide → 2,6-Diethyl-4-methylphenylacetonitrile

HRID 1890227Notes

Reaction equation

HRID 1890227 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([C:6]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH2:15][CH3:16])[C:7]=1[CH2:8]Cl)[CH3:5]>O.C(#N)C>[CH2:4]([C:6]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH2:15][CH3:16])[C:7]=1[CH2:8][C:1]#[N:2])[CH3:5]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 667076972,6-Diethyl-4-methylbenzyl chloride

Product 1

HCID 667077002,6-Diethyl-4-methylphenylacetonitrileYield 115.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
75 °C

Procedure

In a mixture of 50 g of water and 99 g of acetonitrile was dissolved 27.98 g of sodium cyanide. To this mixture, a solution of 157.18 g of 2,6-diethyl-4-methylbenzyl chloride (GC-area: 71%) in acetonitrile (293 g) was added dropwise at 75° C. over 2.5 hours. This mixture was stirred at 75° C. for 3 hours. To the reaction mixture was added 99 g of water, and the mixture was separated. The organic layer was concentrated. To the residue were added 99 g of water and 198 g of hexane and the mixture was separated. The organic layer was washed with 99 g of an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated to obtain 123.46 g of 2,6-diethyl-4-methylphenylacetonitrile (GC-area: 71%) as a brown oil.

Workup

  1. customthe mixture was separated
  2. concentrationThe organic layer was concentrated
  3. additionTo the residue were added 99 g of water and 198 g of hexane
  4. customthe mixture was separated
  5. washThe organic layer was washed with 99 g of an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b84433f24697484bbcd3de91fe4f3ff4
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

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