PolytheneSam
(Master Searcher)
09-01-01 22:27
No 209429
      nitroalkanes  Bookmark   

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
(Hive Addict)
09-02-01 02:58
No 209462
      Re: nitroalkanes  Bookmark   

  US4319059 is cool shit. So, obtaining the nitroethane, nitropropane, etc. from the reaction mixture is as easy as crashing it out with dH2O?
[image]

  I'm going to help all of you cleanse this diseased planet.
 
 
 
 
    PolytheneSam
(Master Searcher)
09-02-01 18:22
No 209605
      Re: nitroalkanes  Bookmark   

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
(Chief Bee)
09-03-01 02:26
No 209717
      Re: nitroalkanes  Bookmark   

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
(Hive Addict)
09-03-01 13:56
No 209817
      Re: nitroalkanes  Bookmark   

PolytheneSam, do have refs for the rxns from lactic acid-- through to product? 
 
 
 
 
    WizardX
(Wizard Master)
09-05-01 18:45
No 210535
      Re: nitroalkanes  Bookmark   


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.

 
 
 
 
    PolytheneSam
(Master Searcher)
09-05-01 18:57
No 210536
      Re: nitroalkanes  Bookmark   

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
This looks interesting, too.  http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0401
 http://www.orgsyn.org/prep.asp?prep=cv4p0573


http://www.geocities.com/dritte123/PSPF.html
 
 
 
 
    obituary
(Hive Addict)
09-05-01 20:50
No 210574
      Re: nitroalkanes  Bookmark   

alpha halo acids
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0115