A (mostly) kitchen friendly synthesis of 2c-b

[malesh67482]

Hi @Swirly! Great write up!

1. For re-x of the nitrostyrene, is plain methanol recommended?
2. Are you advising against using oxalic acid for the clean up after the reduction?

 

[Swirly]

1. For 2,5-dimethoxynitrostyrene use plain methanol, for 3,4,5-trimethoxynitrostyrene use IPA.
2. I believe that there are more disadvantages to oxalate than advantages, the major advantage is that it does make for a very clean final product. The disadvantage is that yields seem to suffer.
For both 2-h and mescaline, next time I would make the sulfate and then convert to HCl.

I had both my 2c-b and mescaline tested at kykeon and both are totally pure. I made my last mescaline with the oxalate step and it is a white batch instead of my older yellow ones where I made HCl then did an A/B to another HCl.

LIke I wrote maybe you will include the oxalate and do it better than me, yields won't suffer.

 

[Rabidreject]

Really? That’s interesting. When I made mescaline it was totally glimmering white, iv heard others say similar to you though.
I am wondering if its because I have a propensity towards making sulfate salts as opposed to HCl?

In fact everything iv reduced using the NaBH4/ copper method has come out bright white and all been sulfate

Shouldn’t really make a difference but I dunno.
I did make some slightly off white stuff the first time, because when I removed the IPA I was left with like a black nasty colour but then I figured out if I properly purified my nitroalkene the organic layer was a beautiful straw Color.

 

[Swirly]

Yes, I have not made the sulfate yet, but next time I sure will. But not as the final product, final product will be HCl.

 

[Rabidreject]

Can I ask why that is? Why not the sulfate salt as final? Simply the difference in weight?

 

[Rabidreject]

Oh also how about the in situ bromination using NaBr?
I get that NBS is like a really easy way of brominating but it involves me buying extra stuff I potentially don’t need lol

Also I figure if it’s this easy to brominate 2c-h would it potentially be just as easy to iodinate it using iodine crystals and H2O2 in an acidic environment? Something I want to try…

 

[Rabidreject]

I found I got pretty good yields using this technique for the 3,4,5-aldehyde as well... At first I was getting this weird ‘cottage-cheese’ looking by product but I was just adding too much EDA. Purity was fantastic though, without even doing a re-x I ended up getting 70-75% yields on the next part. This was obviously not on large scale though, a tenth or so of what u did here so yeah maybe you would lose a lot of yield at scale (I dunno I don’t do bulk)
I am waiting for more borohydride to come and it’s annoying me - I wish I hadn’t reduced the md-p2np I last did as I would have been able to do this instead and I actually take 2c-b, as opposed to the md compounds which was curiosity

 

[Rabidreject]

I’m confused.
Iv done the reduction reaction on 3 or 4 different nitroalkene’s now and the reaction has been great every time.
This time, when I got to salting it out - nothing happened and it neutralised really quick
I’m a little confused.
At the end of the reaction the organic layer separated nicely so I added a little more base and separated and all that bollocks.
I had some issues with solubility when I tried to salt MDA directly out of isopropyl so I evaporated most of the iso and topped up with acetone and proceeded to salt using sulfuric and nothing crashed out. Then it just neutralised really quickly as well.

The nitrostyrene I was reducing looked like it was really nice quuality so I’m really confused…

 

[Rabidreject]

Oh and I used a 7.5 mol eq of NaBH4 and a 0.1 mol eq of CuCl2.

It’s just weird because usually when a reaction goes wrong there is some sort of sign that it’s behaving strangely before the salting bit.

Guess I’ll try it again

 

[Rabidreject]

Hmm I find myself wondering if the freebase crashed out of the isopropyl whilst I was evaporating it and then wouldn’t re dissolve in the acetone. Think maybe that might be the case.

 

[Rabidreject]

Oh okay you can basically forget all that! Ha
I stuck it in the freezer and had nice fallout.

I guess 2c-h sulfate is significantly more soluble in acetone than other compounds I have worked with thus far. Interesting

 

[Swirly]

Don't use acetone, use ethyl acetate!

 

[Rabidreject]

Yeah I clocked that in the end funnily enough. Ended up using ethyl acetate in the end anyway, or was that for the 2c-b salting I ended up doing. F knows. Either way I would use it in future for both these.
Mescaline works really well with acetone though which is why it was my go to at first.

 

[Rabidreject]

Man I swear every time you do a reaction you learn something new. Even if it’s the same reaction with a differing reagent…

I love it

 

[Rabidreject]

I don’t actually even really like 2c-b so I ended up buying succinimide and then synthesising NBS from it for no reason really - I just used bromine for the bromination of 2c-h and don’t really need more than the gram and a bit I have so decided to just save the rest of the 2c-h and the 2,5-DMONS for when my I2/ silver nitrate comes.