wertfun
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nitropropene via nitromethane?
Any body has info about nitropropene synth. below?
The method is the aldol condensation, using NaOH to condense the aldahyde and nitromethane and then HCL to dehydrate it to the nitropropene
As I know nitropropene with nitromethane gives inactive product.
[Edited on 4-12-2005 by wertfun]
[Edited on 4-12-2005 by wertfun]
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Axt
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General nitroalkane-aldehyde condensation is below. Know nothing on dehydrating it.
| Quote: | To a stirred mixture of 3 moles of nitroalkane (note 1) and 120 ml. of water was added dropwise (note 2) a solution of 3 moles of aldehyde (CH3CHO,
C2H6CHO) and 155 ml. of water during 90 minutes. Small portions of solid sodium carbonate were added from time to time to keep the mixture basic to
litmus (note 3). Stirring was maintained for 2 hours after aldehyde was all added, then the mixture was let stand for 3 hours, ether extracted, and
the ether extract was washed and dried (Na2SO4). The ether was removed and the nitro alcohol was twice vacuum distilled.
Note 1. Three-molar quantities were taken with nitromethane but only one-molar with nitroethane. Note 2. The aldehyde could be added all at once
except in the preparation of 1-nitro-2-propanol. Note 9. The temperature rise was greatest in the preparation of I-nitro-2-propanol, gradually
reaching 60° even with the incremental addition of aldehyde. This reaction mixture alone of the four nitro alcohols prepared became homogeneous as
the reaction progressed.
J. Org. Chem.; 1955; 20(7); 927-936 |
Yield was 70% for nitromethane-acetaldehyde.
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wertfun
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I think we have to wait Darkfire to learn how to dehydrate it.
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sparkgap
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Uh, which of the three nitropropenes did you want? 1- and 2-nitropropene can't be prepared via a condensation reaction.
IIRC, just heating the nitromethane-acetaldehyde would cause spontaneous dehydration to 3-nitropropene, but I'm not really certain...
sparky (~_~)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
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wertfun
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I wanted the the one in the second post( darkfire ) told about it shortly.
http://www.sciencemadness.org/talk/viewthread.php?tid=2908
The first post asked about P2NP. And darkfire answers.
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CherrieBaby
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You can't use this method (or any condensation) to get P2NP with nitromethane, it will give P3NP with nitromethane + phenyl acetaldehyde. Bezaldehyde
+ nitroethane give P2NP.
On the bonus side, if you want the nitrostyrene, you can use MeNO2 with Bezaldehyde to give Nitrostyrene, and that can then be reduced with just
Fe/HCl to phenethylamine, as per: Synthetic Communications, 35, #7, 2005, pp 913-922 - kindly posted by acetate
here: http://rapidshare.de/files/8566503/Synthetic.rar.html
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wertfun
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Thanks for PDF information.
Is it possible to use nitromethane in Urushiraba Method?
[Edited on 6-12-2005 by wertfun]
[Edited on 7-12-2005 by wertfun]
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enima
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why don't you _try_ reading before asking stupid questions.
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enima
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nitromethane in urushibara will result in methylamine being produced.
What would be interesting is urushibara and formic acid.
[Edited on 7-12-2005 by enima]
[Edited on 7-12-2005 by enima]
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wertfun
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thanks
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Ephoton
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I have read this thread a few times and an idea has been growing becouse of it.
3 nitro propene could be used to make one of thouse butyl couterparts for amph
that drone was talking about.
would not the alkene on the end of the chain reduce with the alkene on the nitro carbon.
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