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Filemon
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| Quote: | Originally posted by roamingnome
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Do you know this decarboxylation? I don't know their name. |
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R-COONa + NaOH + CaO + Heat => R-H + NaCO3 |
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It appears here:
http://www.educnet.education.fr/rnchimie/chi_org/viel/acides...
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roamingnome
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That’s a good reference, Ill look into it….
I would say the CaO might be absorbing water, but in an aqueous medium that would make no sense…..
Well I began to sonicate the turbid solution of 25 mls….
But as I lusted for more power I pushed the micotip over 200 watts….
The 120 mm tip was already bent because it was used surplus of course I tried to straiten it, but somewhere after 200 watts it sheared off from the
other body ending the test.
leaving me to search for a titanium rod to thread and replace the aluminum one. I also noticed the machine is not tuned anymore ahhhhh….. I should
have just stuck to yeast….
Anyway…. The smell of the liquid … I simply can not describe it and remain professional in this forum….
I have not smelled phenylethylamine to compare it to….
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CH3CH2COOH + 2 NaOH →CH3CH3 + Na2CO3 + H2O
http://en.wikibooks.org/wiki/Organic_Chemistry/Carboxylic_ac...
ok this is just forming the alkane as understood
( a 2 electron transfer?), but throwing methyl radicals in the mix is of interest...
i need a gamma radiation source probably...
[Edited on 12-6-2007 by roamingnome]
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Filemon
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| Quote: | Originally posted by garage chemist
EDIT: Page 301 in the Gattermann from 1909. Also reduction of benzoic acid to toluene, stearic acid to octadecane, glycerol to propane etc. are stated
as being possible with HI/P.
[Edited on 18-3-2007 by garage chemist] |
Where? There not this. As much as time needs the reduction of the benzoic acid and stearic acid?
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S.C. Wack
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Actually that is on page 302, which is 314 of the .djvu.
Yet when mandelic acid was treated in a somewhat similar way to what Org was saying, the investigators obtained phenylacetic acid instead of
ethylbenzene:
15 grams mandelic acid (0.1 mol) [5], 2.07g KI (6.25% of theory), and 6g Red Phosphorous is dissolved in a solution of 70ml phosphoric acid and 10 ml
of water, and this solution is refluxed for six hours (bp of soln 144°C). After the reaction mixture has cooled down, a little water is added to
dissolve precipitated inorganic salts. The solution is extracted with ether, and the pooled extracts washed with a little dilute NaHSO3, followed by
water, and is then dried over Na2SO4. The ether is removed under diminished pressure and the residue is distilled (bp 138-139 @13mmHg). The yield is
12.5 grams (90%) of phenylacetic acid melting at 76°C. 3.2 grams of phosphorous could be recovered from the aqueous solution.
- http://www.erowid.org/archive/rhodium/chemistry/phenylacetic...
Perhaps a much larger amount of HI and phosphoric acid is necessary.
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Filemon
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Sorry but that it's an example the HI/P doesn't reduce carboxilic acid. Alone it reduces the group hydroxide.
[Edited on 6-7-2007 by Filemon]
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Filemon
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I believe that it could work. But previously it would be necessary to attack with PI3 to make iodide of acid and then to add water to complete the
reduction.
[Edited on 6-7-2007 by Filemon]
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chochu3
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I tried this reaction once and the carboxylic acid was not reduced. I did a reflux and added all reagents as a onepot synthesis, and did not record
the temp. of the reaction.
The follow up rxn I will make HI first then add the Ph-alanine and run the reaction up to 150 celsius under reflux. Any suggestions on how this rxn
should be ran.
According to some references PI3 forms a substitution at the alpha carbon with the halide, so that's what might have happened to my first reaction.
The workup was extracted as any carboxylic acid (metal hydroxide) and then hydrolyzed with muratic acid.
[Edited on 6-7-2007 by chochu3]
\"Abiding in the midst of ignorance, thinking themselves wise and learned, fools go aimlessly hither and thither, like blind led by the blind.\" -
Katha Upanishad
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solo
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| Quote: | Originally posted by chochu3
I tried this reaction once and the carboxylic acid was not reduced. I did a reflux and added all reagents as a onepot synthesis, and did not record
the temp. of the reaction.
The follow up rxn I will make HI first then add the Ph-alanine and run the reaction up to 150 celsius under reflux. Any suggestions on how this rxn
should be ran.
According to some references PI3 forms a substitution at the alpha carbon with the halide, so that's what might have happened to my first reaction.
The workup was extracted as any carboxylic acid (metal hydroxide) and then hydrolyzed with muratic acid.
[Edited on 6-7-2007 by chochu3] |
Question ....did you run you reaction in a sealed container as it was done in the Gatterman example?........solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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chochu3
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no it was refluxed in an open atmosphere no pressure vessels or the like.
\"Abiding in the midst of ignorance, thinking themselves wise and learned, fools go aimlessly hither and thither, like blind led by the blind.\" -
Katha Upanishad
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solo
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You might then try to at least put a ballon on top of the refluxing column to maintain a closed environment as the P&V will adjust with the ballon
.....you might just do it but run it at 160 for 6 hours if you want to get any viable results....tip, after the reaction let it cool and allow the
P&V come to equilibrium at RT then open the vessel under the hood or out in the open for there may be some not healthy gases post reaction.....I
have planned to do the same reaction with a sealed vessel with a pressure gauge and a thermometer in the vessel to monitor the reaction , the vessel
is rated at 60psi ....please report your findings as I will report mine..........solo
[Edited on 6-7-2007 by solo]
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Filemon
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Why the cinnamic acid decompose down for heat (141ºC) in styrene? For double bond in position beta?
[Edited on 9-7-2007 by Filemon]
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Filemon
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I believe that it could decrease phenylalanine with P/I if previously it has transformed to phenylalanine iodide with PI3. But which solvent you could
use? The phenylalanine is alone soluble in H2O. But if phenylalanine iodide was soluble in another solvent it could also be good to make the reaction.
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solo
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In Gattermans study he doesn't mention anything about acid halogens nor esters......I would stay with water.....since it's what's needed to make HI in
situ.........solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Filemon
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chochu3 say that it doesn't work. It's logical according to the theory, HX produces alpha halogens in the carboxilic acid.
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solo
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But did you also read he did it in an open vessel.......not sure of the temp, short in hours.....in order to prove or disprove a study one has to
replicate the conditions in order to comment.
Best thing to do is for me to run my test see what the results come out to be.......solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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solo
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Ready to go with the reaction .....will make the HI first then add the amino acid and allow it to react for 6 hours at 160 C......will post pic of
final reaction.....solo
Shot with FinePix2650 at 2007-07-26
[Edited on 26-7-2007 by solo]
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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chochu3
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here is a pic (attached) of my first reaction setup. the sand bath was at a constant temp. of 145 degrees celsius.
\"Abiding in the midst of ignorance, thinking themselves wise and learned, fools go aimlessly hither and thither, like blind led by the blind.\" -
Katha Upanishad
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jon
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this is the rub, in some papers I've seen on hi reductions alcohols weren't reduced completly until 20 hrs had elapsed (by tlc anal.) so you may have
to run it longer and then there is the stochiometry to consider it takes 6 mols of hi so If you only have one or two floating around it might take
longer to cycle that through.
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Filemon
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I have seen an interesting reaction to reduce a carboxilic acid:
http://www.orgsyn.org/orgsyn/pdfs/CV3P0671.pdf
It should be easier to reduce a ester.
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solo
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The idea is to reduce the COOH down to CH3....as to reducing it from an ester....NaBH4 with ethanol 50%/H2O 50% will reduce the ester with 80+yield in
4.5 hours...better than messing with sodium....would like to hear anyone attempting the reduction of the COOH to the alkane.....I have had problem
with my pressure gauge and I broke my thermometer so until I get a replacement my trial in the bottle will have to wait......solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Sandmeyer
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The issue of reducing phenylalanine to amphetamine has been brought up many times here and elsewhere, to the point of becoming boring. Wetdreams is a
place to discuss repetitive, non-challenging, (meth)amphetamine-cookery topics.
[Edited on 30-12-2007 by Sandmeyer]
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roamingnome
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The use of the criticism “non-challenging” in regards to the thread title is off the mark.
Turning a carboxylate group into an alkane is front line organic transformation. Just because these experimenters are using an amino acid as a test
bed is too much for you?
http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleFo...
Sono-emulsion electrosynthesis: electrode-insensitive Kolbe reactions
Save opinions for the “drug cookery vs. “bomb making” thread
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Sandmeyer
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...and your point with that paper is?
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roamingnome
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It is merely literature that fulfills the requirements of the thread title.
Hexanoic acid a carboxylic acid dimerizes into decane an alkane.
It is also totally unrelated to drugs! Brownie points for me.
Of course if I was feeling theoretically naughty I would try to repeat this experiment with phenylalanine in an excess of acetate ions.
Happy new years to all and good reactions to people that deserve them…
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maniacscientist
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first I was intrigued by an experiment I came across in my college book, which involved Ca-salts of the aminoacid and heat, but will yield the amine
with the c-chain of the other aminoacid attached to the amine group iirc.
[Edited on 3-1-2008 by maniacscientist]
[Edited on 3-1-2008 by maniacscientist]
[Edited on 9-1-2008 by maniacscientist]
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