SM2
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Zingerone
So we extract our ginger ketone, dry, and condence 4.27g in 2M NaOH (aq), with a large abundance of MEK, 50ml min. The flocuent precipitate is
quickly washed with cold water, dried, and dissolved in twice it's weight ethyl methacrylate monomer. The cheapest, easiest neat monoomer tou can buy
from China via Ebay. A homogeneous, slightly straw looking transparent mixture is formed, which does not change, Now, PEA HCL is basified and
washed/dried. 17,24G of the FB in 50ml MeOH, is slowly added to our above straw colored mixture, which over the 10 minute addition, has turned red,
red/yellow, and then a lighter different shade of red. Upon watching, one can see the reddish heavy layer settle. 50ml brine is added, with heavy
magnetic stirring, so the red portion forms small miscles, and eventually emulsify with the whole. Stirring is stopped after 10-15 minutes, and now
the red layer is more defined, but floating on top. It is also cleaner looking. Add 50more ml H20, and finally extract the oil with toluene. First
wash w/ gusto, 25 ML. 2ND WASH ONLY 10ML. 3RD WASH 15ML. Toluene conservation, a treasured OTC soon to go on a national level. Red extract is
gently distilled until almost all the toluene is out, and the toluol is put in a container where it will be reprocessed at some later date, and not
wasted!
Now, this red oil (not turkey red) could be reacted with a degradation product of tyrosine, but that is just the teaser. As it is now, it represents
a very interesting molecule. But I have no GC/MS Quad|||| sitting around, so, I don't know. Und ich denka verleicht etwa could have been lost in
translation. This is the Beginnings section, and here is a beginning.
[Edited on 13-8-2014 by SM2]
"Old men who speak of victory
shed light upon their stolen life
they - drive by night- and act as if they're
moved by unheard music." B. Currie
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Crowfjord
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I'm fairly confused as to what you did (or intended to do) here. Here is my take on the above:
Zingerone was reacted with a large excess of 2-butanone and base (how much 2M sodium hydroxide? Or did you mean 2 molar equivalents?) in water. Then
the butanone adds to the tail of the zingerone twice to make a branched diketone? This is where my confusion begins to crescendo: next a precipitate
(assumed to be the condensation product - likely a mixture) is isolated and washed, but there was no neutralization of the base... So was the product
at this point a non-soluble phenolate? Or other sodium salt?
Then you go on to add ethyl methacrylate. I see how the later added phenethylamine would condense with one or two equivalents of this, but was the
previous branched ketone intermediate supposed to to add to it? Was the (assumed) diketone supposed to cyclize? Etcetera...
Anyways, my curiosity had been roused and wouldn't mind seeing some clarification. Maybe some structures of the intended intermediates and product?
Haha, here's to putting the madness in sciencemadness. Cheers.
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arkoma
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I couldna make heads or tails either, and ginger has been on my list of "interesting" substances to investigate.
Quick question: gingerol alledgedly decomposes to zingerone on cooking. Reflux powdered ginger in nonpolar solvent=zingerone?
"We believe the knowledge and cultural heritage of mankind should be accessible to all people around the world, regardless of their wealth, social
status, nationality, citizenship, etc" z-lib
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Crowfjord
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Not sure about that, but it can be made by condensing acetone with vanillin with a base then hydrogenating the double bond(analogous to the synthesis
of rheosmin AKA raspberry ketone from p-hydroxy benzaldehyde).
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arkoma
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@Crowfjord--I have LOTS of powdered ginger, in fact a 112gm bottle--no vanillin (well, mebbe .3gm ethylvanillin).
And if I had any amount of benzaldehyde..........well, lets say I could do without booze for a while LOL
"We believe the knowledge and cultural heritage of mankind should be accessible to all people around the world, regardless of their wealth, social
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Crowfjord
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Perhaps one could extract gingerol and the related compounds from the ginger with acetone or ethyl acetate and then react with aqueous base to form
zingerone via retro-aldol reaction. Zingerone is "sparingly soluble" in water, according to Wikipedia. I wonder if it could be steam distilled?
Then again, with the other stuff in ginger, it might be better to do a bisulfite extraction or some such after the retro-aldol.
[Edited on 14-8-2014 by Crowfjord]
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arkoma
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I read the wiki too, what got me thinking about it. Zingerone looks VERY interesting to an insomniac LOL. Figured heat from reflux with EtAc would
take gingerol>>>>zingerone? Maybe need pop over to the-collective and ask.....
"We believe the knowledge and cultural heritage of mankind should be accessible to all people around the world, regardless of their wealth, social
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rannyfash
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benzaldehyde can be made from the ozonolysis of styrene, the needed chemicals are very easy to get hold of, one made easily from a cheap readily
available plastic, the other obtained from a cheap ozone generating car lighter thing
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CuReUS
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Quote: Originally posted by rannyfash  | | benzaldehyde can be made from the ozonolysis of styrene, the needed chemicals are very easy to get hold of, one made easily from a cheap readily
available plastic, the other obtained from a cheap ozone generating car lighter thing |
could you be more elaborate about the ozone generator
actually i am interested in the same reaction i.e making benzaldehyde from styrene
the reaction is actuallly ironic ,converting a stinky chemicla like styrene to a nice smelling one like benzaldehyde ,but i guess that's how chemistry
is
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Metacelsus
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Benzaldehyde can also be made by oxidation of toluene (I have done it):
https://www.sciencemadness.org/whisper/viewthread.php?tid=22...
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