Can you not read? Tsathoggua's procedure thus far has been posted in its entirety, in quite considerable detail.

I cannot yet state hi's/it's yield, for the reaction has not yet been brought to its conclusion

His bad, he hadn't noticed that.

Consider his semisarcastic reply retracted, in that case.

IPA could be used, although it would have to bee purchased.

As far as the price tag of the benzaldehyde, it wasn't excessive at all, actually, at least not compared to the worth of the amine, but thats really not the point of what is being done here. The point is to successfully complete the reaction (well, at least, clean up that nitroalkene, the amine catalyst should still be in the methanolic fraction, which has been taken off at the buchner. A quick wash with MeOH spiked with a little GAA is in order he thinks, followed by pure MeOH.

Keeping all the fractions, of course. In the end all the solvent fractions will be stripped and examined for further nitroalkene of a likely lesser purity.

Color is slightly orange when soaking wet with orange MeOH from the rxn pot, drying to citrine/cadmium yellow.
The rxn mixture as stated, has been taken off at the buchner, of course has been saved and shall be evaporated down and shock-crystallized again by freezing. This was started immediately on his waking up, and continued until the workup began, the result was the color of the methanol fraction changing from bright clear yellow, to an orange slurry containing curdy precipitate, which appears to be bright yellow when evaporated.

The unsaturated bond in the nitroalkene should permit staining via iodine vapor, correct?

Will an amine stain with I2? Tsathoggua is hoping the wood-free paper doesn't itself stain.....

You have to embed the direct link: http://img827.imageshack.us/img827/7187/67nitro.jpg

Are these nitroalkenes typically soluable in water?

Aldehyde used is 2,5-MeO-4-Me-PhCHO, nitroalkane added is (currently) MeNO2, although when this is done, EtNO2 condensation shall bee performed.

As far as TLC goes, check your inbox....about those plates. Tsathoggua in this case refers to paper chromatography however, having no plates at the moment.

3g of benzaldehyde was used in the first reaction, so thats approximately 1/3rd yield, however this is not the end yield. There is still significantly more nitroalkene to bee had in the reaction mixture and MeOH washings. Most of the remaining methanol will be distilled off (should be fine at atmospheric pressure, one would think, given the BP of MeOH is only 65 C at 1atm), then the total reaction mixture harvested for recrystallization with a little boiling MeOH.

Is this stuff soluable in dichloromethane? that would allow for taking out the TETA residue easily.

Its being dyscalculic that makes things difficult, I am severely so.

No, I don't know how to calculate %yield.

What further suggested workup here, to remove catalyst? Tsathoggua isn't familiar with the soluability of the nitroalkene product.
Shulgin works up by washing nitroalkene with a little MeOH. Presumably losing product here too.

Some, of course, is ready for reduction. But the rest is still in there, more has crashed out of MeOH rxn fluid, needing filtering off.
Can SOME of that MeOH be removed by atmospheric pressure distillation? obviously too much was used.

Interesting-A second crop has been obtained, via evaporation of a sample of the methanol washings from the original.

The original obtained product is curdy rather than crystalline in nature, and bright yellow this has been set aside in a vial. the orange crystals were obtained via washing this above product with ice cold MeOH and evaporating the washings yield of this looks nice, very nice.

Suggested procedure from here? washing the yellow, curd-like product with cold MeOH through the buchner and collecting whats left? or can this yellow product be reduced directly?

This crop of crystalline material, this, is ready, after trituration under dH2O, Tsathoggua would think, to remove any trace of catalyst, and subsequent drying, for reduction with LAH in THF.

To be quite truthful, ethers, specifically THF and diisopropyl ether, make him much more nervous than LAH does. A lot more so in fact.

He is thinking, of the primary reaction mixture, partially evaporate at atmospheric pressure, AT ROOM TEMPERATURE, then pour the mixture onto salted ice in ice cold brine. The H2O insoluability really is handy....thanks for that info.

As for IPA...the rubbing alcohol here is full of methyl salicylate. All of it, that he has ever seen is contaminated with shite, gah, probably wouldn't get served at the local pharmacy anyway........the pharmacist manager is an obsequious git that slimes and fawns when picking up a prescription, but Tsathoggua went in for some bicarb yesterday, only for (without saying what the use is) had the pharmacist say 'thats the wrong one' and go get the pharmacist, who then spent ages looking for ranitidine (heartburn) despite being informed that ranitidine is not what the customer wanted, 'suggesting' he consults his doctor instead.

Idiot....after about 15 minutes, just about managed to walk out with a small tub of bicarb (100g), the fucker refused to sell the larger one.

Ever heard the phrase 'the customer is always right'? fucker obviously hasn't...hows about learning the phrase 'the customer would happily burn your house down you oily, obsequious, toffee-nosed dogooding twat'

Next reactions shall bee conducted in IPA. Thanks again for that tip. He shall get on to his supplier for some IPA when he has spare money....at the moment he does not, for he is watching an auction on some huge collection of labware he wants that is going at the moment for a rather nice price.....

No idea if methyl salicylate azeotropes with IPA, could always hydrolyse the ester with base though. Anyway, Tsathoggua doesn't like buggering around with OTC solvents...ick! nasty.

He shall have to buy some IPA.

The LAH fires...were they powder fires during transfer to flask, or was it ignition when solvent was added?

Plan is to flame-dry flask, dry THF over NaOH then over lithium (would use Na, but the last experiment towards that.....ooohboy....damn did Tsathoggua ever have to duck fast after his argon line ran dry, spent hours, just to recover a few miserable blobs of Na metal)

Dry solvents prior to use, weigh LAH out under an argon or hydrogen atmosphere. Thinking H2, to avoid buying a new argon tank. Could do the reduction under H2 also for that matter. He would go and attend to it now, but he has a bastard of a headache.....maybe someone he ate disagreed with him.

First LAH reduction yes.

The argon tank ran dry when it was being used as an inert atmosphere for molten salt electrolysis.....understandably, this is messy, when its a molten pool of NaOH and Na, then all that sodium decides it wants to go off like a firecracker.

As for doing the reduction under a H2 atmosphere, this is due to its easy production, and unreactivity towards LAH etc. I take it you are thinking of the flammability of the stuff?

As for alternate reductions, borohydride would be part of a two step process, this is unwanted. Buggering about with Fe/GAA et isn't to Tsathoggua's taste for this, besides, he has neither Fe powder to hand, nor borohydride under his kitchen sink...LAH on the other hand is here and ready to go, as soon as toady recovers from the bastard awful headache he has.


Tsathoggua wonders if lithium, being the beast of a reducing agent it is, might reduce THF....he would imagine though that mere standing over Li prior to use (after predrying of course) wouldn't cause this to a practically important extent.

pyramid is correct. SBH reductions of the double bonds of nitrostyrenes works great. yields are usually stellar and workup is also usually quite nice. you can then reduce the nitroalkane to the amine via Pd/C and ammonium formate CTH (just mix with methanol and let react for a while) or with Zn/HCl, or with Al/Hg or with Raney Nickel, or with LAH or with other stuff. LAH really is a nasty man. If youve never worked with and can avoid it, you should!
ive seen really bad stuff happen with it and used to know 2 chemists, who are deceased now after LAH unleashed her firey fury... I guess it all comes down to how brave/stupid you are and what is it that you are willing to do knowing the risks...