Intergalactic_Captain
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Registered: 4-9-2004
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Alkyl Nitrate to corresponding Nitroalkane?
I'm getting pretty fed up with the assloads of tar that resulting from my attempts to reach an alpha-methylphenethylamine from eugenol. So, I've
decided to try the aldehyde + nitroethane route.
Problem is, I can't seem to find NaNO2 OTC. I can easily make a hundred grams or so of ethyl nitrate, though. The question is, is there any feasible
route out there for the conversion of ethyl nitrate to nitroethane?
If you see me running, try to keep up.
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Nicodem
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Registered: 28-12-2004
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No
Edit:
Well, actually there might be a way, even though it is quite irrational. There is a possibility to use ethyl nitrate as the electrophile in the sodium
nitrite SN2 substitution just like in the nitroethane synthesis from ethyl bromide and sodium nitrite. There are however at least two reasons for
possible failure: 1.) the considerably lower electrophilicity of ethyl nitrate when compared to ethyl bromide; 2.) possible side reactions like the
oxidation of the nitrite anion by the nitrate esters etc.
Mind also that in order to prepare ethyl nitrate one needs conc. sulfuric acid which means it would be more rational to use this in order to prepare
ethyl bromide, diethyl sulfate or monoethyl sulfate salt of sodum or potassium, which all can be used as the electrophiles in the aforementioned
nucleophilic substitution with nitrites.
[Edited on 7-1-2007 by Nicodem]
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