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

Participants

Reaction Steps

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°).

Provenance & Evidence