The Vespiary
The Hive => Methods Discourse => Topic started by: starlight on December 11, 2003, 03:22:00 PM
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is it possible to distill 1-(2,5-dimethoxyphenyl)-2-nitroethane at say 3mm hg?
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Yes, that should be doable. Please report back the boiling point, as it is not recorded in the literature.
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the reason for distilling is that the product of the borohydride reduction was a bright red oil. This was obviously wrong and was probably due to nitrostyrene that was not clean enough. Putting this red oil into a reduction would probably make all manner of goo rather than our desired amine. Similarly I was worried that storing it would lead to degradation, so it was decided to distill straight away.
48g of this red oil was distilled at ~1mmHg (vacuum meter not sensitive enough to give a more accurate reading), and a crystal clear yellow oil distilled over at 142°C. 28g of oil were collected and what looked like 20g of black polymerised crap was left in the distillation flask (I pretty much expected this due to the very dirty nature of the starting material).
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Could you describe its smell?
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I was expecting to get a fruity smell similar to earlier undistilled experiments.
in fact the product was pretty close to odourless which I was surprised at.
the temperature at which the olfactory test was made was around 5 degrees C. I may be able to get more smell of it by warming it - I will see when I return to it.
What were you expecting?
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I have heard unconfirmed reports that the smell would be weakly hydrocarbon-like, something I find strange, as most other methoxybenzene compounds have a more or less strong fruity smell, just as you mention.
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Probably depends on purity, route of synthesis and genetic makeup of the smeller. 2,5-dimethoxythio-ethers made by the shulgin-route have a very light fruit-like smell (reminding of pears or apples), whereas if they're made using buli/alkyliodides they smell like diesel. It's a hint of something sulfourous, not really stenching but not particularly pretty.