Hydrochloric Acid → 4-tert-Octyl-2-nitrobenzene Diazonium Chloride

Participants

Reaction Conditions

Reaction Steps

In a 100-ml flask fitted with a stirrer and thermometer, 15.0 grams (0.06 mole) of 4-tert-octyl-2-nitroaniline is suspended in 20 ml of toluene. To this is added at 25° C. 17.3 grams (0.18 mole) of concentrated hydrochloric acid. The suspension is stirred at 38° C. for 1 hour followed by the addition of 6 ml of water. The mixture becomes thick as the corresponding hydrochloride salt crystallized as a granular precipitate. The mixture is cooled to 0° C. and diazotized by the addition over a period of 30 minutes of 4.3 grams (0.062 mole) of sodium nitrite in 6 ml of water keeping the temperature at -5° C. to -2° C. The mixture is stirred at -2° C. for 1 hour. Two phases occur. The combined phases contain the desired diazonium chloride and are used as is.

Provenance & Evidence