The Vespiary

The Hive => Chemistry Discourse => Topic started by: PolytheneSam on September 01, 2001, 10:27:00 PM

Title: nitroalkanes
Post by: PolytheneSam on 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
Title: Re: nitroalkanes
Post by: Bwiti on 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)

  I'm going to help all of you cleanse this diseased planet.
Title: Re: nitroalkanes
Post by: PolytheneSam on 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
Title: Re: nitroalkanes
Post by: Rhodium on 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.
Title: Re: nitroalkanes
Post by: obituary on September 03, 2001, 01:56:00 PM
PolytheneSam, do have refs for the rxns from lactic acid-- through to product? 
Title: Re: nitroalkanes
Post by: WizardX on 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.

Title: Re: nitroalkanes
Post by: PolytheneSam on September 05, 2001, 06:57:00 PM
I don't have any references on lactic acid or anything on alpha-halo acids.  You might try here. 

http://www.orgsyn.org/orgsyn/orgsyn/fullTextSearch.asp (http://www.orgsyn.org/orgsyn/orgsyn/fullTextSearch.asp)


This looks interesting, too. 

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0401 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0401)


 

http://www.orgsyn.org/prep.asp?prep=cv4p0573 (http://www.orgsyn.org/prep.asp?prep=cv4p0573)




http://www.geocities.com/dritte123/PSPF.html
Title: Re: nitroalkanes
Post by: obituary on September 05, 2001, 08:50:00 PM
alpha halo acids

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0115 (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0115)