Possible Total Synthesis Of Mescaline

[Rhodium]

What's wrong with the Vanillin -> 5-Br-Vanillin -> 5-OH-Vanillin -> 3,4,5-TMB route proposed by me and Osmium four years ago? Everything needed are as good as OTC.

[Aurelius]

Sorry, aurelius missed that one as a result of misreading.  one of the steps leading towards the synthesis MMDA involves nitroethane (hard to get).  However, aurelius was blind and didn't realize that it was the wrong set of steps AND that nitroethane is never needed for PEAs

[yellium]

[pharmacist]
>I hope that I didn't missunderstand your question.

You did. My point is that you just can't attach 3 electronwithdrawing groups like NO2/N=N+ to an aromatic ring
and think that the first one adds as easily as the third one.
When all you've got is a nailgun, every problem looks like a messiah...

[Cyrax]

But having multiple _equivalent_ type of groups on the ring is no problem, they all undergo same reaktions when manipulated, thats a fact...


Yeah right ... check out Vogel's Textbook of practical organic chemistry, 5 the ed., p 1163.  I have a ref. to back up what I am saying: since with multiple amine groups in ortho position on the phenyl group, there may be benzotriazole formation when you do the diazotization: the free electron pair of a not diazotized amine does a nucleophilic attack on a vicinal diazonium ion.
Now, the question is: Do you have one?

[Rhodium]

And for those of you who haven't got that book, it shows the following reaction:

1,2-Diaminobenzene -HNO₂-> Benzotriazole

...effectively outruling the possibility of the sandmeyer reaction on polyaminobenzenes.

[pHarmacist]

Cyrax: please ask me about the refs one more time.. I told you I have NO refs, I came up with this synt on my own... is there any such thing as 3,4,5-triamino-toluene, or is it impossible to synthesize?

One more general point, just a moment ago i saw Assholiums synt on

https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cb.mannich.html

where he is going via Mannich reaction, correct me if im wrong but I see no point in that... If he's going to use NaCN anyways, why not let it preform nuclephilic attack as i described, form nitrile and reduce it with Raney Ni or LAH as described in my original post in this thread ([7] -> [8] -> [9] -> [10]), wouldn't that be easier? I guess it depends, but just a thought...
Never underestimate the power of retrosynthesis.

[Cyrax]

Dude, I can read.

I asked for a ref. about what you were driveling: But having multiple _equivalent_ type of groups on the ring is no problem, they all undergo same reaktions when manipulated, thats a fact...
If what you are saying is a fact, you 'll have to be able to substantiate your argument.

Is there any such thing as 3,4,5-triamino-toluene, or is it impossible to synthesize?  Yeah sure it 's possible to synthesize that compound.  It's just impossible to diazotize all those the amino groups like you suggested.

Or if you don't believe me, be my guest: do the reaction (I suggest at a molar scale).  We see who gets his ass blown up.

You 'd better do a descent literature study, before you post one of your 'great' synthetic pathways in the Serious Chemistry forum.

[Rhodium]

pharma: The reason to use the mannich route is that you don't have to start with a 2-methylhydroquinone derivative to end up with 2,5-dimethoxyacetonitrile (a hydroquinone derivative is enough) and you don't  need NBS.

No synthesis makes another route obsolete, we just add alternative possible ways for us to arrive at our target compound.

[RedMonn_16]