Acetonitrile → Benzonitrile, 2-(4-acetylphenoxy)-5-nitro-

HRID 1155744Notes

Reaction equation

HRID 1155744 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][C:14]([C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)=[O:15].C([O-])([O-])=O.[K+].[K+].C(#N)C>O>[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])=[CH:18][CH:17]=1)(=[O:15])[CH3:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 514854Benzonitrile, 2-(4-acetylphenoxy)-5-nitro-Yield 35.1%

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 (0.05 moles) of 2-chloro-5-nitrobenzonitrile, 7.01 g (0.0515 moles) of 4-hydroxyacetophenone, 7.10 g (0.0515 moles) of anhydrous K2CO3, and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was then 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 twice from 300 ml of absolute ethanol to give 4.95 g (35% yield) of purified 2-(4-acetylphenoxy)-5-nitrobenzonitrile, mp 135°-136.5° 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 twice from 300 ml of absolute ethanol

Sources & evidence

ORD record
ord-7bd88f40e10e4f128932f539ded78713
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

Loading…