Ammonia → (2-Ethoxyphenoxy)acetonitrile

HRID 2308422Notes

Reaction equation

HRID 2308422 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])[CH3:8].Cl[CH2:18][C:19]#[N:20].N>C(O)C.O.CC(C)=O>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:18][C:19]#[N:20])[CH3:8]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 667552-Ethoxyphenol

Product 1

HCID 22280894(2-Ethoxyphenoxy)acetonitrileYield 84.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (550 g, 3.98 mol) was added to acetone (1800 ml) and resulting suspension was stirred for 30 min. 2-Ethoxyphenol (460 g, 3.329 mol) was gradually added under stirring. The mixture was heated to reflux. Chloroacetonitrile (275 g, 3.642 mol) was added and the mixture was stirred under reflux for 24 hours. The reaction mixture was cooled down to room temperature. Solid was filtered off, washed with acetone (750 ml) and combined filtrates were evaporated to give oil. The oil was dissolved in ethanol (180 ml), the solution was heated to reflux and mixture of water (530 ml) and aqueous ammonia (45 ml) was added. The mixture was cooled to 5-10° C. under stirring. Crude crystalline product was filtered, washed with mixture of ethanol (250 ml) and water (400 ml). The crude product was recrystallized from ethanol /water mixture to give pure product (500 g).

Workup

  1. customresulting suspension
  2. stirringunder stirring
  3. temperatureThe mixture was heated to reflux
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 24 hours
  6. filtrationSolid was filtered off
  7. washwashed with acetone (750 ml)
  8. customwere evaporated
  9. customto give oil
  10. temperaturethe solution was heated
  11. temperatureto reflux
  12. additionwas added
  13. temperatureThe mixture was cooled to 5-10° C.
  14. stirringunder stirring
  15. filtrationCrude crystalline product was filtered
  16. washwashed with mixture of ethanol (250 ml) and water (400 ml)
  17. customThe crude product was recrystallized from ethanol /water mixture

Sources & evidence

ORD record
ord-45f0906ff3d2422486357ed74ccb45c2
Source dataset
uspto-grants-2004_12
Patent number
US06835853B2

Reaction notes

Loading…