Nice nitroethane synth by WizardX

[malvaxman]

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/

[Rhodium]

His homepage is linked from my site (as anything else of use).

[uemura]

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

[joyman]

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.