Carbon Tetrachloride → 1-Trichloromethyl-3,4-dinitrobenzene

HRID 903090Notes

Reaction equation

HRID 903090 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](C)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].O(Cl)Cl.[C:17]([Cl:21])(Cl)([Cl:19])[Cl:18]>>[Cl:18][C:17]([Cl:21])([Cl:19])[C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 118833,4-DinitrotolueneHCID 24646Chlorine monoxide

Product 1

HCID 233376401-Trichloromethyl-3,4-dinitrobenzeneYield 96%

Procedure

3,4-Dinitrotoluene (2.49 g 0.0136 mole) and dichlorine monoxide (4.74 g, 0.055 mole) in carbon tetrachloride (50 ml) were heated in a Carrius tube from which air had been removed, as in Example 6 at 75° for 10 hrs. The reaction solution was filtered to remove a white solid (0.35 g) which was identified by its infrared spectra as 3,4-dinitrobenzoic acid. The filtrate was dried (MgSO4) and the solvent removed on a rotary evaporator to give 1-trichloromethyl-3,4-dinitrobenzene as a white crystalline solid (3.57 g, purity by HPLC 96% yield 89.2%). The product was recrystallized from carbon tetrachloride-petroleum ether to give essentially pure product (mp 69.5°-70.6°).

Workup

  1. customhad been removed, as in Example 6 at 75° for 10 hrs
  2. filtrationThe reaction solution was filtered
  3. customto remove a white solid (0.35 g) which
  4. dry with materialThe filtrate was dried (MgSO4)
  5. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-6b67a031a42344ae85aa557f7617c73f
Source dataset
uspto-grants-1980_10
Patent number
US04226783

Reaction notes

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