4-ethyl-2,5-dimethoxybenzaldehyde help…

Rabidreject

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Alright,
So I am working with phenethylamine’s and have made mescaline and reduced quite a few other nitroalkene’s with great yields.
I would like to make some 2c-e and given that I have 2,5-DMOBA, and I only want to make a small quantity so yield isn’t as important to me as flexibility, could I perform a Grignard ethylation on the 2,5-DMOBA?

I understand that people usually start from the acetophenone but I can only buy precursors in large amounts (well large in terms of what I actually need) and it doesn’t make sense to buy a load of that and start from that.

I would react 2,5-DMOBA with EtMgBr (probably as a premade solution) in an argon atmosphere, in an ice bath…

Is this something that is going to work? I’m a little worried about purification but figured the boiling point shouldn’t be radically different to the starting aldehyde - a little higher of course.

I dunno; 2c-e is something I REALLY want to make, iv not consumed any for YEARS (since 2000’s RC times) and it’s probably my favourite psychedelic - CERTAINLY my favourite phenethylamine so far…

I am obviously learning and I figured adding an extra step at the beginning of the process would make sense…

I did look into friedl-crafts alkylation but poo poo’d the idea. I’m sort of hoping this idea is AS MUCH of a poo poo.
As I say, I’m happy to get crap yields as I don’t need much anyway.

I also realised that it’s only when you haloginate at the 4 position, that the NaBH4 / copper catalysed reduction kicks it off - handy for me here…hopefully

If I AM being a mad amateur like a lot of my old posts on here are (which have all been bought up again recently from the restructure) do let me know.
Oh also, what is with this new restructure? You go into phenethylamine’s and it’s just amphetamine and MDMA - c’mon now! 🙄
 

Rabidreject

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Alright you can pretty much ignore this, I understand the best strategy would be to put half my money into the 2,5-DMOBA and half into the acetophenone that is substituted in the same way.
I understand why now….
Thanks for all the help! Ha
 

amieri

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Man was really hoping this thread was going to get some action.hows the project coming along?I hope everything has been great in ur world. mine been a circus of a shit show and am unfortunately on pause at the moment
 

YenaneY

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I'm not sure about it and I personally don't have experience with this synthesis in particular.
And I'm also only learning, but what I thought is benzaldehyde is an electrophile and gringnard reagents are nucleophiles, so I guess there should be a reaction. But I'm not really sure about selectivity.
And this is what I'm not sure about, but I though the substitution would mainly be directed close to the formyl group, but I also read that formyl groups on benzene ring can be directing to para due to resonance, but I'm not sure about that-
 

Rabidreject

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Okay yeah, I did look Into this actually but iv not moved forward with it yet. I do plan to at some point but not like I wrote in this lol

I think the best way is to start from 2,5-dimethoxyacetaphenone - exactly as the one write up covering all the 2c-x substances on here says!
The only reason iv not moved forward is because you need some random chemicals that i would need to custom order or make like hydrazine (would make that) and then dichloromethyl methyl ether and stanic chloride.
I can definitely get them but as I say would need to custom order and then also I would need to order the acetophenone so I’m essentially saving up.

Until then, I can do the haloginated DOX and 4C compounds coz I need to buy less in order to make them!
 

Nicoino

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If you want I can sell custom made 4-ethyl-2,5-dimethoxybetanitrostyrene.
 
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