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Hunterman2244
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[*] posted on 1-10-2018 at 03:05
Mescaline synthesis


I want thinking about glycerin, and though it could be used to methoxylate phenylalanine into mescaline through the decarboclxylation of the intermediate. I was thinking that a Lewis acid could act as catalyst for the reaction. This probably would be no good as a production method, but is is possible? I have no interest in mescaline itself in this case, it just popped into my head as a substrate for the reaction.
EDIT: Aluminum Chloride seems to have the perfect qualities.

[Edited on 1-10-2018 by Hunterman2244]
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Metacelsus
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[*] posted on 1-10-2018 at 09:42


I don't think that reaction will work. Glycerin doesn't add methoxy groups to benzene rings. What would be the mechanism?



As below, so above.
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[*] posted on 1-10-2018 at 10:48


Quote: Originally posted by Metacelsus  
I don't think that reaction will work. Glycerin doesn't add methoxy groups to benzene rings. What would be the mechanism?

Removing electrons breaks the carbon-carbon bonds and forms a positive charge, being acidic it should participate in a sort of Friedel–Crafts reaction. Glycerin can be oxidized to formic acid and further methanol, so it seems it should form the methoxide group on the ring.
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[*] posted on 1-10-2018 at 10:58


This post is deficient on several levels.



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1-10-2018 at 11:04
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[*] posted on 1-10-2018 at 11:08


Quote: Originally posted by JJay  
This post is deficient on several levels.

Why so?
A thought popped into my head, and I wondered if it was possible.
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[*] posted on 1-10-2018 at 11:17


A case of fractal wrongness (https://rationalwiki.org/wiki/Fractal_wrongness).
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[*] posted on 1-10-2018 at 11:18


If people shared every thought that popped into their heads on here, the stacks of nonsense unreferenced reactions would be piled even higher than the spam. As Metacelsus inquires, what is your proposed mechanism for this reaction? Your second response is extremely vague and doesn't answer anything. Remove electrons from what? Break which carbon-carbon bond? What is acting as an oxidizing agent? Also formic acid is definitely not "oxidized to methanol," that's a reduction.

It looks like you are taking snippets of true things and putting them together the wrong way, like the blind men trying to figure out what an elephant is.




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[*] posted on 1-10-2018 at 12:50


Man this shit is so wrong in so many motherfucking levels yo:P

[Edited on 01/10/18 by fusso]




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[*] posted on 1-10-2018 at 13:33


Quote: Originally posted by Texium (zts16)  
If people shared every thought that popped into their heads on here, the stacks of nonsense unreferenced reactions would be piled even higher than the spam. As Metacelsus inquires, what is your proposed mechanism for this reaction? Your second response is extremely vague and doesn't answer anything. Remove electrons from what? Break which carbon-carbon bond? What is acting as an oxidizing agent? Also formic acid is definitely not "oxidized to methanol," that's a reduction.

It looks like you are taking snippets of true things and putting them together the wrong way, like the blind men trying to figure out what an elephant is.

I explained it to the best of my ability. A covalent bond is shared electrons. Removing those electrons causes the bond to break. In glycerin there is a chain of three bonded carbons. I never meant to imply oxidation of formic acid, I was just using similar reactions to help explain the idea.
It has nothing to do with being misinformed, I had a thought and it seemed important. So I shared it to get people's opinions.

The glycerin forms formic acid, which makes formate groups on the phenyl ring. Those are reduced to methoxide. Does that help?

Instead of saying how wrong something is, explain why. If you can see the problem then just say what it is. I went in knowing it was probably wrong, but not why.

[Edited on 1-10-2018 by Hunterman2244]
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[*] posted on 1-10-2018 at 13:45


What would remove the electrons and thereby breaking the bonds (strange way to look at it, but ok)? How would formate react (if it would form in the first place) with the now open places on the benzene? What would reduce the formate?

You can't just count some atoms, throw them together and make up some way they will react.
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clearly_not_atara
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[*] posted on 1-10-2018 at 13:48


Dude, you really need to start way earlier in the orgchem textbook. None of that makes any sense.

For one thing, oxidants don't "remove electrons" like you pulled them out with a pair of tweezers. Oxidizing glycerol with nitric acid produces mesoxalic acid, and none of the carbon-carbon bonds break. But oxidizing it with sodium periodate produces a mixture of formaldehyde and formic acid.

Also, if your "mechanism" has oxidation and reduction happening to the same molecule in the same flask, it's wrong.

Also, you can't reduce a "formyl" to a "methoxy" because that would require changing the order of the bonds, from O-C-Ar to C-O-Ar. Instead, formyl is reduced to "hydroxymethyl" or "carbinol".

Furthermore, formic acid does not participate in Friedel-Crafts formylation reactions, because it instead decomposes to carbon monoxide under this condition.

Sigmatropic is right about fractal wrongness. The more you explain yourself, the less sense you're making. I think you'll be capable of learning chemistry, but you need to start by admitting that you don't know hardly any chemistry right now.

[Edited on 1-10-2018 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 1-10-2018 at 14:51


I am not arguing why some reaction would happen. I thought of something and wanted to know if it is possible. There is no wrong only a question on a possibility.
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[*] posted on 1-10-2018 at 15:06


Quote: Originally posted by Hunterman2244  
I am not arguing why some reaction would happen. I thought of something and wanted to know if it is possible. There is no wrong only a question on a possibility.
You need to grow up and be able to admit you got stuff wrong. Everyone makes mistakes. Including me. (One time I suggested that hydrochloric acid and hydrogen peroxide could be safely combined. They can't. Epic fail, atara very dumb.)

The "chemistry" you've proposed in this thread bears only a superficial resemblance to actual chemistry. You are and have been wrong about numerous things in every post you've made in this thread. You can learn from your mistakes and get better, or you can continue on the path you're on, which is to repeatedly deny your own ignorance and keep pretending until you become too deluded for anyone to communicate with.

Just be a little more humble. Everyone is wrong sometimes.




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 1-10-2018 at 15:11


Quote: Originally posted by clearly_not_atara  

Also, if your "mechanism" has oxidation and reduction happening to the same molecule in the same flask, it's wrong.


I know you've heard of disproportionation...
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[*] posted on 1-10-2018 at 16:27


Quote: Originally posted by happyfooddance  
Quote: Originally posted by clearly_not_atara  

Also, if your "mechanism" has oxidation and reduction happening to the same molecule in the same flask, it's wrong.


I know you've heard of disproportionation...

https://www.youtube.com/watch?v=hou0lU8WMgo




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 1-10-2018 at 16:52


Quote: Originally posted by clearly_not_atara  
Quote: Originally posted by Hunterman2244  
I am not arguing why some reaction would happen. I thought of something and wanted to know if it is possible. There is no wrong only a question on a possibility.
You need to grow up and be able to admit you got stuff wrong. Everyone makes mistakes. Including me. (One time I suggested that hydrochloric acid and hydrogen peroxide could be safely combined. They can't. Epic fail, atara very dumb.)

The "chemistry" you've proposed in this thread bears only a superficial resemblance to actual chemistry. You are and have been wrong about numerous things in every post you've made in this thread. You can learn from your mistakes and get better, or you can continue on the path you're on, which is to repeatedly deny your own ignorance and keep pretending until you become too deluded for anyone to communicate with.

Just be a little more humble. Everyone is wrong sometimes.

The whole fucking point of this was that it was wrong, I wanted to know why. You can read my posts and consider what they say. You did The same thing, took a snippet out of context. The quote is not saying I was right, it was to point out that it was a question. I wanted to know why or why not. Instead of trying to argue with literally nothing, why not just help?
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[*] posted on 1-10-2018 at 17:51


I did read your post. Others have already given pretty sound reasons for why what you presented was wrong. It's kinda hard to explain all of it in a concise way that would be meaningful for you when it's clear that your knowledge of the basic concepts of organic chemistry is lacking. There isn't a problem with that, but you should go and start with the basics, as clearly_not_atara suggested instead of getting defensive.



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[*] posted on 1-10-2018 at 20:47


Quote:
it was a question


The analogy I want to use is pottery.

When you make something out of clay, first you put it together, and then you fire it in the kiln. Chemistry is like this: first you arrange the reagents, then they react. What you've asked is, basically, why can't I modify something (the structure of glycerol) while I'm reacting it with something else (phenylalanine). And the answer is that it's in the kiln! You can't perform two reactions at once because the reagents for the different reactions will start to react with each other. It's like trying to modify a piece of clay while you're firing it: it doesn't work that way. Every time you want to change it, you have to take it out of the kiln and cool it off (extraction and isolation).

This is the biggest problem with your post, because it's a fundamental fact about all chemical reactions that people have to absorb before they can start trying to synthesize anything. It takes a while to really internalize this rule, and usually the only thing that does it is practical lab experience.

Once you start to look at chemistry in a properly step-wise manner, it becomes obvious why what you're proposing doesn't make any sense. If you have to break apart the C-C bonds in glycerol and then extract and isolate the product before you do anything else with it, you might as well start with methanol!

The other big glaring issue is that you think Friedel-Crafts reactions can attach oxygen to benzene, but in reality they only attach carbon atoms to benzene. Mescaline has oxygen atoms attached to benzene. If you have a formyl benzene with a structure like (Ar-C-O), it will never rearrange to a structure like (Ar-O-C) unless you use a rearrangement reaction (in this case, the Dakin reaction, but the result is a phenol).

Adding to the trouble, Friedel-Crafts reactions with AlCl3 cannot be performed on phenylalanine at all. In this case, I leave it to you to learn why.

You just can't ask a question this advanced starting from a position of such total ignorance. You need to learn the fundamental rules of organic chemistry in order to be able to make sense of anything.

"Philosophers often behave like little children who scribble some marks on a piece of paper at random and then ask the grown-up "What's that?" - It happened like this: the grown-up had drawn pictures for the child several times and said: this is a man, this is a house, etc. And then the child makes some marks too and asks: what's this then?"

It's nothing, see?


[Edited on 2-10-2018 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 1-10-2018 at 22:45


i don't want to be harsh like the others but think it like this: you are playing chess, and you hypotized a plan to check the other king, the problem is in your plan you move the pieces in impossible ways because you don't know well enough the rules, that's why the others said that nothing had sense of what you said, you wanted to move the horse across the board in une step

[Edited on 2-10-2018 by Ubya]





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[*] posted on 2-10-2018 at 02:55


Quote: Originally posted by clearly_not_atara  
Quote:
it was a question


The analogy I want to use is pottery.

When you make something out of clay, first you put it together, and then you fire it in the kiln. Chemistry is like this: first you arrange the reagents, then they react. What you've asked is, basically, why can't I modify something (the structure of glycerol) while I'm reacting it with something else (phenylalanine). And the answer is that it's in the kiln! You can't perform two reactions at once because the reagents for the different reactions will start to react with each other. It's like trying to modify a piece of clay while you're firing it: it doesn't work that way. Every time you want to change it, you have to take it out of the kiln and cool it off (extraction and isolation).

This is the biggest problem with your post, because it's a fundamental fact about all chemical reactions that people have to absorb before they can start trying to synthesize anything. It takes a while to really internalize this rule, and usually the only thing that does it is practical lab experience.

Once you start to look at chemistry in a properly step-wise manner, it becomes obvious why what you're proposing doesn't make any sense. If you have to break apart the C-C bonds in glycerol and then extract and isolate the product before you do anything else with it, you might as well start with methanol!

The other big glaring issue is that you think Friedel-Crafts reactions can attach oxygen to benzene, but in reality they only attach carbon atoms to benzene. Mescaline has oxygen atoms attached to benzene. If you have a formyl benzene with a structure like (Ar-C-O), it will never rearrange to a structure like (Ar-O-C) unless you use a rearrangement reaction (in this case, the Dakin reaction, but the result is a phenol).

Adding to the trouble, Friedel-Crafts reactions with AlCl3 cannot be performed on phenylalanine at all. In this case, I leave it to you to learn why.

You just can't ask a question this advanced starting from a position of such total ignorance. You need to learn the fundamental rules of organic chemistry in order to be able to make sense of anything.

"Philosophers often behave like little children who scribble some marks on a piece of paper at random and then ask the grown-up "What's that?" - It happened like this: the grown-up had drawn pictures for the child several times and said: this is a man, this is a house, etc. And then the child makes some marks too and asks: what's this then?"

It's nothing, see?


[Edited on 2-10-2018 by clearly_not_atara]


Misunderstanding my point.
Tangental analogy about what you misunderstood.
So asking a question about something I don't know is somehow proposing an impossible synthesis.
Phenylalanine is unrelated, it was just an example of the transformation I was describing. Same with the Friedel-Crafts. Just something related.
You seem to take me as an idiot. This question has no relevance to my knowledge in chemistry. A simple piece of knowledge was missing, so I asked about it.
If you learn division, and are never told that you can't divide by zero, then you will think about dividing by zero.
Flat out calling me stupid doesn't help.
I have no interest in this conversation. It has devolved nothing.
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[*] posted on 2-10-2018 at 04:34


Quote: Originally posted by Hunterman2244  
Misunderstanding my point.
Tangental analogy about what you misunderstood.


If anyone misunderstood you, it was because what you were saying was very unclear.
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[*] posted on 2-10-2018 at 05:29



Quote:

Phenylalanine is unrelated, it was just an example of the transformation I was describing. Same with the Friedel-Crafts. Just something related.


the post is about an idea you had, using glycerin to methoxylate phenylalanine, and you mentioned the Friedel-Crafts reaction to "prove" or hypothesize the use of glycerin as a viable option, so if all of this unrelated to your question, what was you question??? how to turn something into mescaline using glycerin?





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[*] posted on 2-10-2018 at 09:08


I hate to point out the obvious also, but a lot of members here (including myself) regret the unfortunate fact that our common hobby attracts many who are in it for no good reason (namely to make drugs). If you really want to approach the subject for scientific reasons, why don't you call your molecule 3,4,5-trimethoxyphenethylamine so that at the very least it doesn't attract unwanted negative attention? Additionally, there are many people (like myself) that would know right away what molecule you were talking about if you had said 3,4,5-trimethoxyphenethylamine; whereas I needed to refresh myself as to what mescaline is.
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[*] posted on 2-10-2018 at 09:38


Detritus?



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[*] posted on 2-10-2018 at 18:20


Quote: Originally posted by happyfooddance  
I hate to point out the obvious also, but a lot of members here (including myself) regret the unfortunate fact that our common hobby attracts many who are in it for no good reason (namely to make drugs). If you really want to approach the subject for scientific reasons, why don't you call your molecule 3,4,5-trimethoxyphenethylamine so that at the very least it doesn't attract unwanted negative attention? Additionally, there are many people (like myself) that would know right away what molecule you were talking about if you had said 3,4,5-trimethoxyphenethylamine; whereas I needed to refresh myself as to what mescaline is.

I don't know, I just wanted to use what I thought would be something people know about, rather than something more obscure like 345 trimethoxy phenyl propanoic acid or something, as the reaction substrate. And to be fair a lot of drug chemists(not meth-shake and-bakers) are moderately smart people, so any help is still help. Mescaline really doesn't have much appeal to drug chemists anyways, because of cacti.
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