single digit gram scale.

Does conducting the nitroaldol condensation in GAA as opposed to the appropriate nitroalkane work well for this?

It would be very nice to be able to use GAA, rather than nitro, for the experimenter. He doesn't really fancy using his precious R&D puriss-grade nitromethane and nitroethane for a mere solvent, that, in his opinion, and mine, is tantamount to pharmaceutical blasphemy.

2,5-MeO-4-CH3-1-phenyl-2-nitropropene and nitrostyrene.

That sounds real sweet.

Why cooling? I have only ever seen reflux attempted before. Have results been contrasted between reflux (in GAA or THF?)
Not, that the experimenter wants to open his new THF.....that stuff isn't something he is particularly comfortable around.

So far, so good, he just had some arrive, in a plastic bottle with literally all the air squeezed out of it. But opening and closing a bottle of any sort of ether isn't something this experimenter likes doing, for obvious reasons. I.E explosive diarrhea, the diarrhea coming shortly after the peroxide explosion, from fright after narrowly managing to throw himself clear of the potential fireball

Thing is, its a 'gift from the eastern europe fairy' and its uninhibited, and as such might just go and peroxidise faster than a paki with a backpack full of chupatti flour. The experimenter at the moment lacks the EDA to make EDDA (question, pyramid, you say 500mg of ethylenediamine was added, do you mean ethylaminediamine? or was that a typo for EDDA, I think it pertinent to ask, seeing as how there has been very little mention of EDA and much of EDDA in this thread)

I thank thee, on behalf of my experimenter komrade, he is most pleased to read this.

Makes him wonder, if the solvent alcohol is important, he cound scrounge some IPA, just about, and not very much of it, for its electronics grade stuff, expensive, and not readily parted with by the person who has some, however the experimenter has a pissing cuntload of MeOH, at least 20 liters hanging about, and some ethyl acetate he could hydrolyse to EtOH/NaOAc using NaOH (come to think of it, that is exactly what he might just do, when he has finished his bottle of jamaican coconut rum )

He doesn't mean to be a pain in the arse asking me too many questions which I need to find answers to, but I am starting to want to poke him in the eye and tell him to get the fuck on with it. I don't think he has any EDA hanging around, but sodium hydroxide and GAA are at his fingertips, as is TETA, or ammonium acetate.

He might try with TETA-tetraacetate, on a small scale, via titration of some TETA freebase to neutral point in a very little THF, using GAA (under a pad of argon of course, nobody likes peroxides, well, muslims aside;))

Of course if the yield is better than that with the EDA/EDDA (whichever you did mean) no need for him to place a test tube under his pillow at night and hope the eastern europe fairy comes and leaves him some EDDA, but otherwise.....

As an aside...hows about plain vanilla benzaldehyde (pun intended, ish), PhCHO that is, not vanillin? reacted with nitroethane, using EDA or EDDA?

No methylamine at hand, although could be easily made, I am sure he is a decent enough chemist, although not particularly talented, to pull a JennyMcCarthy's minge-smelling rabbit out of the nitromethane hat, one quick wave of his zinc wand, accidentally knocking some GAA over, and hey, it just might happen for the fucker.

Thanks for the info re:addition of GAA before catalyst.

Out of academic interest (the experimenter and the lovecraftian toad-god both are that, and then some, although you wouldn't pull it out of the stereotype hat at first, not until you saw him spinning round/rocking back and forth) what is the mechanism for this polymerisation, and how does the acidic environment slow or eliminate this?

He was thinking of preforming the acetate salt of TETA by titrating some of the freebase to neutrality with GAA, dissolving in a few ml excess GAA, and adding thusly.

TLC is regrettably, not.

Much to his regular frustration, he can't afford plates atm.

Tsathoggua, dont use nitroalkanes as solvents. ipa, methanol, ethanol are good solvents for nitroaldol/elimination.
generate the ammonium salt of your choosing in the alcohol. use 5-10mol% of ammonium salt per mol of aldehyde, 1.1-1.2mol of nitroalkane.
first do a small run without reflux with your choice of ammonium salt. check yield after 24 hours. if not satisfactory, try again, same amounts, but reflux now for 1 hour or more. check for yields. if still not satisfactory, switch to a different ammonium salt.
on a side note doing chemistry without some sort of analytical tool (tlc, hplc, gc, etc...) is like trying to drive blind with the gps on. you get the instructions, but you cant really see what you are doing.

tlc plates arent expensive. they can be had on ebay for cheap. I have a couple spare packs if you want, just pm me, im giving them off for cheap.

I've seen the price of plates on ebay....I almost got some, then realised that I couldn't even close to afford it, reading the fine print

Check your inbox...

Figures, given the finer division of the metal.

In the end, Tsathoggua, I do believe went with TETA-tetraacetate in MeOH solution brought down to PH 3.5 with GAA.

From the brief glimpse I got, before his formless spawn buggered off with it into the darkness (why, I wonder, wrap it in tinfoil, when its pitch-black down there in the bowels of the earth...odd) it had turned a brilliant clear yellow color, which given the known property of the nitro group and nitroalkenes in general of that nature, has to be a good thing.

65% for PhCHO? not good enough for his standards, methinks.

That said, not too bad at 15 eur/250ml. If it was one of the more expensive aldehydes then that would be absolutely unacceptable.

3g aldehyde (60mmol), a fine white crystalline powder, odourless and tasteless, displaying a very, very faint trace of highlighter pen-dayglow yellow-green under the light of a sodium lamp, dimmer switch turned right down (preferred for tsathoggua's bedroom, he really dislikes the light produced by those foul energy savers, uggh, and for that matter, they are most offensive to my own sensory apparatus) was dissolved in 40ml MeOH, perhaps 150-200mg refused to solvate, so a little heat was applied, bringing it up to 37 degrees C, with shaking.

While this was solvating on the hotplate, a formless spawn carefully rendered to PH 3.5, using GAA, in mililiter aliquots, constantly measured via an electronic PH pen, a methanolic solution of triethylaminetetramine freebase, possibly a little old, translucent yellow in color, a thick liquid with a scent that I am reliably informed, is quite reminiscent, although faintly, of popcorn, possibly of the toffee variety.

A quantity of this solution (2g in 40ml MeOH total) was added to the reaction flask in a quantity sufficient to equal 600mg of TETA base equivalent. This was added at first a 5ml or so portion, under monitoring using an infrared thermometer gun, upon realising that a rise in temperature was not going to take place, this was added to the now room temperature (22 degrees C) solution of 2,5-dimethoxy-4-methylbenzaldehyde in MeOH, followed by a small excess (2.48g) of nitromethane (Merck, analysis by GCMS >98%, specific gravity 1.143-1.138-) in sufficient methanol to bring the total volume up to 70ml. This was agitated, and left to stand exposed to the light for a short time, perhaps 5-10 minutes, whilst tsathoggua packed up his lab glass, blasted the reagents out of his PH pen with the garden hose before rinsing with distilled water, and returned his reagents to the appropriate places. The reaction flask was then jacketed in aluminium foil and allowed to stand at room temperature.

A pale yellow color rapidly evolved on addition of the nitroparaffin, which on last inspection some 6-7 hours later, was observed to have deepened to a crystal clear topaz-yellow color, before rapidly being returned to the foil surrounding.

Tsathoggua will dig out some watercolor paper and attempt a paper chromatography analysis tomorrow, and sooner or later he shall send for some EDA one of the formless spawn and compare yields.

Unless however, the yield from the TETA is stellar, upon that instance, of course, there shall be no requirement for EDA.

Unless yield is poor, the analogous condensation shall bee performed with nitroethane (Merck, GCMS assay->97%)

Quick question-molar fraction calc. correctly? 60mmol? or is it 6mmol, or 60? it is one of those, that much I can tell. I THINK I reported it correctly.