B-nitro-2,5-dimethoxystyrene? Or something along those lines…

[Rabidreject]

Okay, so I tried the nitroaldol reaction using ethanol as the solvent as I don’t have huge amounts of nitromethane to use as solvent as well.
I stupidly refluxed for only two hours, not realising that the shulgin method from which the guy whose video I was watching took it from, was also using NM as the solvent, using ammonium acetate? From what I can remember.

Anyway long story sort of short, I can’t get it to crystallise - which is leading me to think the reaction didn’t run to completion given that styrene’s are meant to be super easy to X’stalise…

I only have a shit hotplate - the cheap one that almost everyone buys from china (SM2 or someshit - iv seen it under different brands but the front panel is either blue or red and it’s like 10cmx10cm) sort of all beyond the point and honestly I dunno if it would even go up to 101c, probably tbf but either way that wasn’t the issue here,
I only refluxed for two hours and then just stirred at RT all night but as I say, when poured over ICY ICY COLD isopropyl, it didn’t crash out. It’s currently in the freezer but clearly something isn’t right as everyone always mentions how easy it is to crystallise these bad boy molecules!

I guess the reason I mentioned my hot plate is I just bought a new heating mantle because when I bought mine, I was so enamoured by the digital temp display that I forgot to actually check it had a friggin’ mag stirrer! It was a serious annoying situation.
To be fair, i actually haven’t needed a mantle with a stir bar until now as I have only done cold, reductive amination of tryptamine into various psychoactive ones.

I have been sort of trying to move onto the nitroaldol reaction with 2,5-TMOBA or 3,4,5-TMOBA, in order to make my own phenethylamines as well…

I particularly wanted to mess around with the ‘scaline compounds as iv never tried any…

It may be a little overload for this thread but I will admit I tried some TLC for the first time yesterday.

I made a mix of 8:2 ethyl acetate: methanol and used it for my mobile phase.
I got a plate (only realised a couple of things after I had actually done it, like holding the plates by the edges like an old school photograph) but I also probably didn’t ‘spot’ small enough as I just used a capillary tube without holding a torch to the middle and pulling to make a micro pipette or whatever they are called…
Oh yeah shit I also left it in the developing tank for too long, didn’t realise you were supposed to pull It out before it covers the whole plate…

So I am aware that I need to practice my TLC before trying…really anything, again tbf…

So I guess after all of that, it’s a bit of a stab in the dark asking you guys why it’s not crystallising!!

One thing I love about organic chem is the catch 22 of needing a seed crystal of a substance that won’t crystallise, in order to get it to crystallise…lol

 

[Rabidreject]

Oh yeah I also added enough nitromethane for 10g of aldehyde and accidentally added 5g…

I think I’ll try it again…this time ACTUALLY looking at the numbers! Ha

What an idiot…

 

[Rabidreject]

Also I’m using ethylenediamine as the catalyst…

 

[Rabidreject]

Will try again with ammonium acetate tbf…

Unsure about solvent really. I may just have to bite the bullet and use the nitromethane. It’s just expensive and annoying because i can only get it 40% w/w with any solvent I choose - so I chose DCM, which worked well and I got a fair amount, however, it takes time and effort to continuously distil shit as opposed to ordering it pure!

 

[FENTAMAS]

Try to include in your posts separate detailed but as short as possible description of chemical procedure that you followed - that's how in scientific world we share information.
So that likely your problems will be more obvious and will solve faster.
You can drop me pm in Session for the help with this step if you wish, till you don't fucked up all aldehyde.

 

[Rabidreject]

Much appreciated. To be honest, a lot of what iv been learning has been through chatGPT and then looked up (usually on here, if I can’t find a free paper) to confirm what iv learnt is actually true.
I believe I may have added too much methanol and not refluxed long enough.

Today, I have been practicing stretching out capillary tubes and spotting and general TLC…on substances I KNOW are clean.

So I just spotted a plate with 2x spots of the 2,5-DMOBaldehyde and then two spots of tryptamine (I was going to use another aldehyde but yeah) and it seemed to work a lot better than the other day.

I actually think the issue with the synthesis was probably more a case of it being dissolved in way too much solvent, making it hard to re-x - I guess if I had reduced it under pressure after the reflux it may have worked…

Either way, I have found a work up on here using ethylenediamine and IPA as the solvent- I know a lot of people use ammonium acetate and GAA but I figured it would probably smell more than the ethylenediamine. Could be wrong but anything with ammonia in, does usually stink and so yeah.
I didn’t realise it was fairly standard practice to add both catalytic amounts of ethylenediamine AND GAA….

Anyway yeah I probably will get in touch with you if the area’s in which I think I fucked up, I correct and still can’t work it out. If that’s okay…

Funnily enough I just helped someone cross the line with their n,n-DMT reductive animation from tryptamine and so I like the way what goes around comes around.

If I do message anyone I’ll clean it up and number any questions - I do feel like I should probably try it once more, only correcting the things where I think I went wrong before I contact anyone.

I just have a couple questions re: TLC - ooo that rhymed lol