nitroalkanes

PolytheneSam · September 01, 2001, 10:27:00 PM

While searching nitroethane in the US patent literature I found these patents which look interesting.

4319059 XCH3COOH + NaNO2 --Mg++--> CH3NO2
4431842 ROH + HNO3 --CaCl2--> RNO2
4073798 MDA related compounds (amines and nitro compounds) made from benzaldehydes and nitroalkanes
4015011 Benzaldehyde and nitroalkane synth, Pd reduction, Eph and halo-Eph compounds reduced
4004023 MD-PNPs insecticidal

http://www.geocities.com/dritte123/PSPF.html

Bwiti · September 02, 2001, 02:58:00 AM

US4319059 is cool shit. So, obtaining the nitroethane, nitropropane, etc. from the reaction mixture is as easy as crashing it out with dH2O?
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000209429-file_5ism.gif" title="View this image">

I'm going to help all of you cleanse this diseased planet.

PolytheneSam · September 02, 2001, 06:22:00 PM

I saw a post by Rhodium before on this type of reaction. Alpha-haloalkanoic acids generally aren't OTC, but don't seem to be watched either. Also, lactic acid might be easily converted into its alpha-halo form. The possibilities......
If you're interested in nitroethane.

http://www.geocities.com/dritte123/PSPF.html

Rhodium · September 03, 2001, 02:26:00 AM

Yes, right! I didn't think of lactic acid as a precursor, but as you say, it is a good alternative. There is also the reaction (in Org. Syn. f ex) which produces alpha-bromo derivatives of carboxylic acids using PBr3, either as is, or using red P + bromine.

obituary · September 03, 2001, 01:56:00 PM

PolytheneSam, do have refs for the rxns from lactic acid-- through to product?

WizardX · September 05, 2001, 06:45:00 PM

There is also the reaction (in Org. Syn. f ex) which produces alpha-bromo derivatives of carboxylic acids using PBr3, either as is, or using red P + bromine.

Rhodium: Vogel has a many procedures in synthesizing alpha-bromo derivatives of carboxylic acids.