Carbon Tetrachloride → 4-(Trichloromethyl)benzonitrile

HRID 903093Notes

Reaction equation

HRID 903093 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.O(Cl)Cl.[C:13]([Cl:17])(Cl)([Cl:15])[Cl:14]>>[C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:13]([Cl:17])([Cl:15])[Cl:14])=[CH:2][CH:3]=1)#[N:8]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7724p-TolunitrileHCID 24646Chlorine monoxide

Product 1

HCID 2855444-(Trichloromethyl)benzonitrileYield 100%

Procedure

p-Tolunitrile (4.10 g, 0.035 mole) and dichlorine monoxide (6.93 g, 0.074 mole) in carbon tetrachloride (97 ml) were added to a bottle under nitrogen. The bottle was capped and stored at room temperature for 4 days. The water layer was separated, the organic layer dried (MgSO4) and the solvent removed on a rotary evaporator to give p-cyanobenzotrichloride as an oil (7.87 g, yield 100%). The oil was combined with a similar run and distilled in a short path still to give a white crystalline solid which was recrystallized from petroleum ether to give substantially pure p-cyanobenzotrichloride (mp 40.5°-41.7°).

Workup

  1. customThe bottle was capped
  2. customThe water layer was separated
  3. dry with materialthe organic layer dried (MgSO4)
  4. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-457d37dc9ac24f6fa9fd2749cb69a1af
Source dataset
uspto-grants-1980_10
Patent number
US04226783

Reaction notes

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