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?


  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