Author Topic: nitroalkanes  (Read 2120 times)

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PolytheneSam

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nitroalkanes
« 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


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Bwiti

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Re: nitroalkanes
« Reply #1 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?


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

PolytheneSam

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Re: nitroalkanes
« Reply #2 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.

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Rhodium

  • Guest
Re: nitroalkanes
« Reply #3 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.

obituary

  • Guest
Re: nitroalkanes
« Reply #4 on: September 03, 2001, 01:56:00 PM »
PolytheneSam, do have refs for the rxns from lactic acid-- through to product? 

WizardX

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Re: nitroalkanes
« Reply #5 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.


PolytheneSam

  • Guest
Re: nitroalkanes
« Reply #6 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


This looks interesting, too. 

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


 

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




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obituary

  • Guest
Re: nitroalkanes
« Reply #7 on: September 05, 2001, 08:50:00 PM »