Acetonitrile → Benzonitrile, 2-(3-methoxyphenoxy)-5-nitro-

HRID 1155743Notes

Reaction equation

HRID 1155743 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 514844Benzonitrile, 2-(3-methoxyphenoxy)-5-nitro-Yield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen bubbler were placed 9.13 g (0.050 moles) of 2-chloro-5-nitrobenzonitrile, 6.39 g (0.0515 moles) of 3-methoxyphenol, 7.10 g (0.0515 moles) of anhydrous potassium carbonate (K2CO3) and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was cooled to room temperature and diluted with 150 ml of water. The product separated as a solid. The solid was filtered off, washed thoroughly with water, and air-dried. The air-dried solid was recrystallized from approximately 200 ml of absolute ethanol to give 7.15 g (53% yield) of purified 2-(3-methoxyphenoxy)-5-nitrobenzonitrile, mp 102°-103.5° C.

Workup

  1. customIn a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser
  2. customfitted with a nitrogen bubbler
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customThe product separated as a solid
  6. filtrationThe solid was filtered off
  7. washwashed thoroughly with water
  8. customair-dried
  9. customThe air-dried solid was recrystallized from approximately 200 ml of absolute ethanol

Sources & evidence

ORD record
ord-30318fb5a8a7416b8ef50a0ef4c7409a
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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