Nitroethane synth by WizardX (Post No 206924)
A variant synthesis of nitroethane is:
1) CH3CH2COOH + Cl2 ==>> CH3CH(-Cl)COOH + HCl
2) CH3CH(-Cl)COONa + NaNO2 ==>> CH3CH(-NO2)-COONa + NaCl
3) CH3CH(-NO2)-COONa + H2O ==Heat==>> NO2CH2CH3 + NaHCO3
Some questions:
What yeld could be expected? It should in step 1 even form some di-chloro and maybee some trichloro compounds, right? So how do one know when to stop gassing?
..does anyone have the URL to WizardX´s homepage?
thank you for your help/
:)
His homepage is linked from my site (as anything else of use).
malvaxman,
This is known as the Kolbe Nitroalkene synthesis. The shorter the alkene, the better the yield. Uemura thinks Gattermann-Wieland gives yields for CH3NO2 around 40%, for nitroethane is definitly less (perhaps only 20%).
Carpe Diem
The first step is the Hell-Volhard-Zelinskii reaction alpha-halogenation ... reaction requires Phosphorus (hard to get otc!!) trihalide (generated in situ?) and an excess of halide gas/liquid. The halide first substitutes the carboxyl carbon then gets shifted to the other alkyl carbon.