Water → 4-Isopropylphenylacetonitrile

HRID 1272425Notes

Reaction equation

HRID 1272425 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C-:12]#[N:13].[Na+].O>CN(C)C=O>[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][C:12]#[N:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 749164-Isopropylbenzyl chloride

Product 1

HCID 1382224-IsopropylphenylacetonitrileYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 100 g of 4-isopropylbenzyl chloride in 1500 mL of N,N-dimethylformamide was added 32.0 g of sodium cyanide under ice-cooling. The mixture was stirred at 70° C. for 4 hours, and water was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 96.5 g of (4-isopropylphenyl)acetonitrile.

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b2f0622264f4a188a6d8962ecce7d41
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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