Moiety
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Vanillin to Zingerone to Raspberry Ketone
I have a pretty simple question.
I plan on using the condensation of vanillin and acetone to make zingerone (this just takes a reflux with NaOH IIRC), which looks very much like the
compound raspberry ketone, save for the methoxy group on the 3 position.
Would refluxing the compound in HBr remove the methoxy group while leaving the ketone intact? My gut would say yes, but I don't know...
P.S. I have been a long time lurker (2+ years), and just wanted to say how glad I am to finally be a part of the community.
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Adas
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HBr will probably not be able to remove the methoxy group. It will rather do something to the ketone group.
What's Wikipedia's opinion about making it?
"In acetone and sodium hydroxide, 4-hydroxybenzaldehyde can form the α,β-unsaturated ketone. This then goes through catalytic hydrogenation
to produce raspberry ketone. This method produces a 99% yield."
[Edited on 17-12-2011 by Adas]
Rest In Pieces!
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Nicodem
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Synthesis of 3-(p-Hydroxyphenyl)-2-Butanone "raspberry ketone"
Ozonelabs- Synthesis of Raspberry Ketone
By UTFSE you can find a few other threads with related topics.
Quote: Originally posted by Moiety  | | Would refluxing the compound in HBr remove the methoxy group while leaving the ketone intact? My gut would say yes, but I don't know...
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What is the reference claiming that HBr can remove the methoxy group? It simply makes no sense. It is well known that refluxing anisols in HBr causes
their demethylation. No demethoxylation has ever been mentioned in any of the hundreeds reports of this type of demethylation method. If
demethoxylation of anisols would be possible this way, you can be sure it would be something widely known.
Also, obviously enones are anything but robust substrates for something like heating in hydrobromic acid.
| Quote: | | P.S. I have been a long time lurker (2+ years), and just wanted to say how glad I am to finally be a part of the community. |
Welcome to the forum. Since you say you are a long time lurker, I will not waste time explaining why this thread belongs to the Beginnings section,
where referenceless threads are better tolerated.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Nicodem
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Thread Moved
17-12-2011 at 10:30 |
Moiety
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I totally understand moving this, in fact, after I posted it I thought to myself if it was in the right place. I have done very little research on
this, I just thought I would post to see what you all thought. After using the search I can see that I am clearly not the first.
When I thought of de-methoxylation you are right Nicodem, I was actually thinking of demethylation.
What do you mean by:
| Quote: |
Also, obviously enones are anything but robust substrates for something like heating in hydrobromic acid.
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? I have only been through one semester of Organic.
Would I get something like this if I were to reflux the enone with HBr? While I realize it isn't raspberry ketone, the dihydroxy compound might be
interesting, and would be a lot easier for me to make than the raspberry ketone.
edit: forgot the picture
Then, an SnX reaction with NaOH could yield this:
I'm really more interested in the chemistry rather than the product...
[Edited on 17-12-2011 by Moiety]
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