easy, crappy nitroethane synth from TsOEt

[psyloxy]

EtNO2 from TsOEt / NaNO2

My french skills: zero + cracked babylon translator

On fait chauffer 186g TsOMe avec 69g NaNO2 au réfrigérant direct et recueille
la mélange, se composant d'eau et de MeNO2. Ce dernier forme une couche
inférieure qui es séparée de léau, lavée et séchée avec Na2SO4. Le produit est
distillé dans le vide et fournit du MeNO2 pur. Si on remplace dans cet essai le
TsOMe par TsOEt, on obtient le EtNO2, mais le rendement laisse beaucoup à
désirer.

Short, probably incorrect translation: heat TsOMe with NaNO2. MeNO2 distills over with H2O. MeNO2 forms the bottom layer. This is separated from the water, washed, dried and vac. distiled to afford pure MeNO2. If TsOEt is used in place of TsOMe, EtNO2 is the product but in considerably less yield.

Somehow my little brain doesn't want to take that as the last word of wisdom. Hey, it's from 1926! They make EtNO2 from NaSO4Et, in nearly acceptable yield, so why not from TsOEt ,too ?

Ref: Rodionow; Bull.Soc.Chim.Fr; 1926,4,39; p318

[psyloxy]

Can't anyone contribute a more educated translation ? The first sentence really puzzles me. They first say heat, then they say cool - i figured this could only be a distillation setup but they could have meant something entirely different. Clarification, anyone ?

--psyloxy--

[hypo]

they are talking about a condenser.
(btw: i guess the first TsOEt should probably be a TsOMe)

[psyloxy]

Merci beaucoup!

So it really is that simple. Make TsOEt from TsOH and CH2(COOEt)2, then destructively distill TsOEt with NaNO2 to get a small yield of EtNO2. Could be the case that 1Kg of TsOH is needed to make 100ml of EtNO2, but given the recyclability of the TsOH and the simplicity of the process, it's worth a try I guess...

--psyloxy--
error corrected...

[Blind_Angel]

On fait chauffer 186g TsOMe avec 69g NaNO2 au réfrigérant direct et recueille
la mélange, se composant d'eau et de MeNO2. Ce dernier forme une couche
inférieure qui es séparée de léau, lavée et séchée avec Na2SO4. Le produit est
distillé dans le vide et fournit du MeNO2 pur. Si on remplace dans cet essai le
TsOMe par TsOEt, on obtient le EtNO2, mais le rendement laisse beaucoup à
désirer.

can be translated in:

We heat 186mg of TsOMe with 69g of NaNO2 in a condensator and we keep the mix, composed of water and MeNO2. This last form an inferior layer that can be separated from water, washed and dried with Na2SO4. The product is vacuum distilled to produce pure MeNO2. If we replace in this essay the TsOMe by TsOEt, we obtain EtNO2, but with very low yield.

[hypo]

psyloxy's translation was better. (actually it was pretty much perfect)

[Blind_Angel]

sorry, actually my english skill seem to be still lacking a lot...