Acetonitrile → 2-Methoxy-1-methyl-4-(4-nitrophenoxy)benzene

HRID 1023518Notes

Reaction equation

HRID 1023518 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].C(#N)C.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 9590p-FluoronitrobenzeneHCID 151030153-Methoxy-4-methylphenol2×

Product 1

HCID 672363822-Methoxy-1-methyl-4-(4-nitrophenoxy)benzeneYield 95.3%

Procedure

To a solution of 4-methyl-3-(methyloxy)phenol (Intermediate 18, 0.800 g) in dry acetonitrile (60 mL) potassium carbonate (1.600 g, 11.58 mmol) and then 1-fluoro-4-nitrobenzene (817 mg, 5.79 mmol) were added and the reaction mixture was refluxed for 6 hours. The solid was filtered off and the solvent evaporated affording the title compound (1.43 g) as an orange solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 hours
  2. filtrationThe solid was filtered off
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-4812a054ac724d14828f02a9b7a11a2b
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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