Hydrochloric Acid → 2-Chloro-3-phenyl-propionitrile

HRID 485219

Reaction equation

HRID 485219 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:8].Cl.[NH2:10][C:11]1C=CC=[CH:13][CH:12]=1.N([O-])=O.[Na+].C(#N)C=C>O.CO>[Cl:8][CH:12]([CH2:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]#[N:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 7855AcrylonitrileHCID 8870Benzenamine hydrochloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 2552722-Chloro-3-phenyl-propionitrileYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

55.8 g (0.6 mol) of aniline and 200 ml of a 25% hydrochloric acid aqueous solution were mixed to obtain a suspension of aniline hydrochloride. While cooling this solution to a temperature of from 0° to 10° C. from outside and stirring it, a solution prepared by dissolving 42.5 g (0.615 mol) of sodium nitrite in 85 ml of distilled water, was dropwise added over a period of about 4 hours. After the completion of the dropwise addition, the reaction mixture was stirred for about 1 hour at a temperature of from 0° to 10° C. To this solution, 200 ml of methanol and 95.4 g (1.8 mols) of acrylonitrile were added, and while stirring the mixture under cooling, 5 g of cuprous oxide powder was gradually added. The reaction mixture was stirred at a temperature of from 10° to 20° C. for 4 hours, and then methanol and unreacted acrylonitrile were distilled off by distillation. The residual solution was separated into an aqueous phase and an organic phase. The organic phase was subjected to distillation under reduced pressure, whereby 87 g (yield: 88%) of α-chloro-β-phenylpropionitrile was obtained. (b.p.: 105°-110° C./4 mmHg).

Workup

  1. customto obtain
  2. temperatureWhile cooling this solution to a temperature of from 0° to 10° C. from outside
  3. customa solution prepared
  4. additionwas dropwise added over a period of about 4 hours
  5. additionAfter the completion of the dropwise addition
  6. stirringthe reaction mixture was stirred for about 1 hour at a temperature of from 0° to 10° C
  7. stirringwhile stirring the mixture
  8. temperatureunder cooling
  9. stirringThe reaction mixture was stirred at a temperature of from 10° to 20° C. for 4 hours
  10. distillationmethanol and unreacted acrylonitrile were distilled off by distillation
  11. customThe residual solution was separated into an aqueous phase
  12. distillationThe organic phase was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-86aa23cfaf114fa2ad840a4b3e9d6610
Source dataset
uspto-grants-1985_08
Patent number
US04536342

Linked notes

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