Carbon Tetrachloride → 2-(Trichloromethyl)benzonitrile

HRID 903092Notes

Reaction equation

HRID 903092 reaction equation
[C:1]1(C)[C:2]([C:7]#[N:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.O(Cl)Cl.[C:13]([Cl:17])(Cl)([Cl:15])[Cl:14]>>[Cl:14][C:13]([Cl:17])([Cl:15])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[N:8]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 107212-MethylbenzonitrileHCID 24646Chlorine monoxide

Product 1

HCID 3052852-(Trichloromethyl)benzonitrileYield 100%

Procedure

o-Tolunitrile (1.83 g, 0.0156 mole) and dichlorine monoxide (6.79 g, 0.078 mole) in carbon tetrachloride were heated at 75° for 18.5 hrs in a Carrius tube following the procedure described in Example 6. The reaction mixture was dried (MgSO4) and the solvent removed on a rotary evaporator to give a white crystalline solid (4.09 g, purity by HPLC 85.45%, yield 100%). The product was combined with that of a similar run and recrystallized from cyclohexane to give substantially pure 2-trichloromethylbenzonitrile mp 98.9°-100° C.

Workup

  1. dry with materialThe reaction mixture was dried (MgSO4)
  2. customthe solvent removed on a rotary evaporator
  3. customto give a white crystalline solid (4.09 g, purity by HPLC 85.45%, yield 100%)
  4. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-49eb5252b28a42e59dcb67985fd8a077
Source dataset
uspto-grants-1980_10
Patent number
US04226783

Reaction notes

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