Water → 4-Isopropylphenylacetonitrile

HRID 229594

Reaction equation

HRID 229594 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-9df1e22e76ea4d78b29edcb781d8aa95
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Linked notes

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