Diethyl Ether → (2-Methyl-3-nitrophenyl)acetonitrile

HRID 1106739Notes

Reaction equation

HRID 1106739 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].[C-:13]#[N:14].[Na+].CCOCC>CN(C)C=O.[I-].[Na+]>[CH3:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:13]#[N:14]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 108947alpha-Chloro-2-methyl-3-nitrotoluene

Product 1

HCID 13530896(2-Methyl-3-nitrophenyl)acetonitrileYield 70.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Chloromethyl-2-methyl-3-nitro-benzene (25 g) was dissolved in 125 ml of N,N-dimethylformamide. To this mixture was added 10.89 g of sodium cyanide (Mallinckrodt, Paris, Ky.) and 0.4 g of sodium iodide (Mallinckrodt) and the heterogeneous mixture was heated to 80° C. for 21 hr. The reaction mixture was cooled to room temperature, poured into ether, washed several times with water, dried, and evaporated. The residue was purified by flash chromatography on silica gel eluting with dichloromethane, giving 16.83 g of (2-methyl-3-nitro-phenyl)-acetonitrile as a cream solid. ##STR118##

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed several times with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-61c896262b104246b15801fbc6b02c9d
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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