Reaction CXIX.—Action of Silver Nitrite on Alkyl Halides

Reaction CXIX. Action of Silver Nitrite on Alkyl Halides. 

This is an important method of preparing aliphatic nitro compounds. Preparation 239.—Nitromethane. 

44 gms. (slight excess) of dry silver nitrite (see p. 517) are mixed with an equal bulk of dry sand and placed in a reflux apparatus 41 gms. (1 mol.) of methyl iodide are gradually added, and the whole heated on a water bath for 2 hours. The mixture is then distilled from a water bath, the fraction 95°—101° being separately collected. It is redistilled over silver nitrite to remove the last traces of iodide. 

Nitromethane can also be prepared by the action of sodium or potassium nitrite on the corresponding salt of monochloroacetic acid. (O. S., III., 83.) 

ClCH2C00Na + NaN02 - N02CH2C00Na -f NaCl N02CH2C00Na + H20 - N02CH3 + NaHC03. 

---