DECOMPOSITION OF THE DIAZO COMPOUND
(1) With n-Butyl alcohol in the presence of sodium carbonate.
A portion of the dry diazo compound was placed in a flask connected with a reflux condenser, and solid sodium carbonate and n-butyl alcohol added. No reaction took place at ordinary temperature so heat was applied. Decomposition started at 65° and evolution of hydrogen proceeded evenly and smoothly until all the diazo compound had disappeared. The alcohol, at first colorless, became an orange and finally a brown color. The solution was then refluxed an hour to ensure complete decomposition of the diazo compound. The smell of an aldehyde was evident indicating that the hydrogen reaction was taking place; the solution was tested with Schiff’s reagent and with ammoniacal silver nitrate with distinct positive results in both cases, showing aldehyde was present. The alcoholic solution was filtered from the sodium carbonate remaining, and the alcohol distilled off on an oil bath. A yellowish-orange porous solid was left in such a small amount that no derivatives could be made and studied. It was free from the diazo compound, shown by its giving no color with an alkaline solution of H acid.