ChemRaver
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Methylenation of Toluene
I was studying the following molecule
http://www.sigmaaldrich.com/catalog/product/aldrich/284548?l...
This is probably a very noobish question but could Toluene be considered a substituted Catechol?
Catechols, which are very similar in structure to Toluene can be Methylenated for instance by reacting with DCM(or DBM) in a basic environment.
For instance:
| Quote: |
Catechol (1,2-dihydroxybenzene) is reacted in a basic solution with dibromomethane(or dichloromethane) to 1,2-methylenedioxybenzene.
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Could this also go:
| Quote: |
Toluene (Methylbenzene) is reacted in a basic solution with dibromomethane(or dichloromethane) to 3,4-(Methylenedioxy)toluene. |
Perhaps I've oversimplifying the chemistry here, but this did strike me as curious, and it seems like it could be possible.
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Paddywhacker
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> Perhaps I've oversimplifying the chemistry here, ...
No, you are raving.
You can see, if you draw out your proposed reaction, that your product contains two oxygen atoms, but your starting materials contain none.
> This is probably a very noobish question but could Toluene be considered a substituted Catechol?
Not in any sense that a normal person would apply.
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smaerd
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It scares me that you (ChemRaver) recently made a post about using 300g of LAH for some type of reduction on an organic substrate. You display a lack
of understanding pertaining to organic synthesis, even on a fundamental level. Yet you have claimed to have been doing chemistry for the past 3
years... Please learn the principals behind the reactions you day-dream, other-wise anything you end up attempting may be quite dangerous. Also, the
way you have prompted your question is a bit bizarre... Most of the time when people ask a 'theoretical question' they propose why they think it
should happen, rather then replacing a completely different reactant and a product name in a quoted sentence.
For example:
| Quote: | | Perhaps I've oversimplifying the chemistry here, but this did strike me as curious, and it seems like it could be possible. |
Why does it 'seem' like it could be possible?
To iterate the answer to your question: no, there is no reason that I can see why any type of methylenation reaction would occur from what you
propose.
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ChemRaver
before giving me free advice, consider that I am doing chemistry for the money
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I was simply asking.... Give me a break. I never claimed to be an expert on this subject. I DID post this in the beginner section. Hence the reason I
am asking here.
Could someone instead of criticizing me for trying to learn, actually point in the direction of understanding the mechanics of why the methylenation
reaction of Catechol happens in the first place?
There clearly is some way for this 3,4-(Methylenedioxy)toluene molecule to be synthesized simply for the fact that it exists and is sold in bulk for a
not much higher price than Toluene. I could easily go buy this from China if I really wanted to but I am interested in how it is synthesized. Forgive
me for being curious.
Yes I am not an organic chemistry expert. You shouldn't feel smart for pointing that out. It should be obvious in the fact that I am posting this
here. What other ways are there that a Methylenedioxy group can be added to toluene?
I've noticed that catechol' can be synthesized from Toluene. Catechols can be methylenated and apperently so can Toluene according to the above, real,
molecule. My question is, if Toluene is not methylenated by the same mechanism, then by who is it methylenated?
[Edited on 14-12-2013 by ChemRaver]
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hyfalcon
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looking at the patents involving the 3,4-(Methylenedioxy) group and interesting substance pops up: piperonal
Now just what does that bring to mind?
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TheChemiKid
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Hint Hint
BLACK PEPPER
Spoon-feeding complete
[Edited on 12-14-2013 by TheChemiKid]
When the police come
\( * O * )/ ̿̿ ̿̿ ̿'̿'̵͇̿̿з=༼ ▀̿̿Ĺ̯̿̿▀̿ ̿ ༽
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ChemRaver
before giving me free advice, consider that I am doing chemistry for the money
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It is true this molecule is only a couple of reactions away from being Piperonal, though that doesn't change anything about the scenario.
I'm starting to get the feeling some of the people here know a lot more trolling than they do chemistry. If I was interested in making something out
of this molecule(3,4-methylenedioxytoluene) I could get it from China and go from there. It's not illegal in any country. Clearly manipulating this
molecule for my own purposes beyond that point is something I am not interested in. I am interested in figuring out how it can be synthesized.
I did exhausted searches of patents and was unable to find any mention of this molecule in particular, inspite of an abundance of
3,4-methylenedioxybenzaldehyde's (piperonal).
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ChemRaver
before giving me free advice, consider that I am doing chemistry for the money
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Okay this thread can be closed.
I found out what I was asking is indeed possible since both catechol and toluene are benzene derivatives. Apparently the inferences I was drawing
about how closely this molecules are related was correct. According to some patents this methylation of catechols by methylene chloride in the
presence of a strong base applies not only to catechols but a great number of substituted benzene derivatives, which, toluene is. My inference seems
to be correcta bout how closely these molecules are related. 1,2-methylenedioxybenzene in comparison to 3,4-methylenedioxytoluene.
[Edited on 14-12-2013 by ChemRaver]
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DraconicAcid
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Quote: Originally posted by ChemRaver  | I was simply asking.... Give me a break. I never claimed to be an expert on this subject. I DID post this in the beginner section. Hence the reason I
am asking here.
Could someone instead of criticizing me for trying to learn, actually point in the direction of understanding the mechanics of why the methylenation
reaction of Catechol happens in the first place? |
Catechol is a phenol- it has hydroxyl groups on an aromatic ring. These can be deprotonated to give a phenolate anion, which can in turn react with
an alkyl halide to be alkylated. Because catechol has two hydroxyls next to each other, they can both react with the same alkyl dihalide, giving you
methylenation.
Toluene has the aromatic ring, but doesn't have any hydroxyls. It is much harder to deprotonate (can't be done in aqueous or alcoholic solution), and
can't be alkylated the same way, let alone methylenated.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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zed
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You wanna know how the material is made. Inquire with the manufacturer. Generally, they are happy to tell a prospective purchaser about their
products.
Otherwise, use the search engine. Go to Rhodium. Use Wiki. Some things are possible, and some things are not.
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smaerd
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Was I trolling or asking you if you had come up with a reason as to why the reaction you proposed was possible? I actually thought about it and
couldn't see it. I'm sure there is a way from toluene to the target compound, it just isn't as you had proposed...
No your inference was not correct, which also means you do not realize why, which again means you should do some reading on organic chemistry.
Hexamethylbenzene is also a substituted aromatic. That doesn't mean it will react the same way as catechol, benzoic acid, or aniline which are also
substituted aromatics. Looks like DraconicAcid covered what you were asking.
It's not about being 'smart' and definitely not a trolling effort. It's about knowing what you're doing when you're dealing with chemicals, I.E. being
a chemist. Learning how to propose questions in a constructive manner generally requires some preliminary knowledge on the subject. That's something
that is encouraged even in the beginnings sub-forum. Go figure I look up the target compound and it's a drug precursor, explains everything including
the user-name...
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Fantasma4500
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wonder if people with general interest in chemistry are more prone to fall victim for SAD.. always such... short temper on SM in winther periods of
what i understand..
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smaerd
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I'm just holding posters to the same level that was/is expected from me. Definitely not angry. New members tend to get these types of posts so that
they learn ways to create constructive discourse rather then spoon-feeding and a lack of genuine interest in the subject matter that they inquire
about. Normally posts similar to these result in a UTFSE or detritus type response. Suppose you're right, I haven't been terribly happy lately. Not
due to the lack of sunshine though... I'll refrain from responding until the weather in my head subsides  .
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DraconicAcid
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| Quote: Originally posted by Antiswat | | wonder if people with general interest in chemistry are more prone to fall victim for SAD.. always such... short temper on SM in winther periods of
what i understand.. |
If I'm feeling short-tempered, it's probably because I'm an academic, and it's exam time.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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hyfalcon
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I just have a thing about feeding cooks. If they want the knowledge, let them read and understand on their own. If they can't do it on their own,
they don't need to be cooks in the first place.
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turd
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If only you had the same thing about feeding trolls.
For some reason this must be one of the most easily trolled forums. It's so weird because scientists are supposed to possess the ability of critical
thinking. Seems like the "anti-cook" smugness interferes with that.
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palico
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Where the oxygen would come from ?
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