Water → 2-(5-Methoxy-4-methyl-2-nitrophenyl)acetonitrile

HRID 881611Notes

Reaction equation

HRID 881611 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH3:12].ClC1C=CC(O[CH2:19][C:20]#[N:21])=CC=1.CC(C)([O-])C.[K+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[C:7]([CH2:19][C:20]#[N:21])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 6435201-Methoxy-2-methyl-4-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 216711082-(5-Methoxy-4-methyl-2-nitrophenyl)acetonitrileYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methoxy-2-methyl-4-nitrobenzene (0.4 g) and (4-chlorophenoxy)acetonitrile (0.4 g) in N,N-dimethylformamide (10 mL) was added potassium tert-butoxide (0.3 g) under ice cooling and this mixture was stirred at the same temperature for 1 hours. This mixture was poured into water and the resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.2 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a4d374ab63a14bd3b6a4d08b8b983207
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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