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Author Topic: Phenylpropionic acid synthesis question  (Read 127 times)

heisenberg

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Phenylpropionic acid synthesis question
« on: December 06, 2009, 01:52:53 AM »
I am looking into the easiest methods to synthesize phenylpropionic acid. The probable starting material would be a benzaldehyde, which would then be used to form a cinnamic acid. The tricky part is the reduction of the cinnamic acid using OTC materials.

If a solid and easy synthesis could be found, it would open up the ability to make various substituted indanes (2-aminoindane, MDAI, jimscaline, etc.). Phenylpropionic acids can be readily cyclized to form 1-indanones, which to me look like a very good starting point for aminoindanes. It is also possible to cyclize phenylalanine derivatives into 2-amino-1-indanones using a similar method, although the nitrogen must be protected. I will post the articles supporting this once I finish purging them of metadata.

Aminoindanes are quite legal so far, and the series has not been completely explored by human test subjects. Only a few in the series have been bioasseyed, with varying results. In any case, I believe they show great promise as possible "drugs of tomorrow".

So, I ask the question: what do you guys think is the best/easiest way to reduce a cinnamic acid to a propionic acid?
I spent all my money on booze and hookers, the rest I wasted - Charles Bukowski

shroomedalice

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Re: Phenylpropionic acid synthesis question
« Reply #1 on: December 06, 2009, 04:21:35 AM »
birch :)

use EDA or if you have the guts (and the stupidity) hydrazine (anhydrous) for your amine solvent.

sodium will not work with EDA but lithium will.

indanyls are not as good as they are made out to be I belive.

they dont have the right dopamine serotonin ratios.

SOMA

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Re: Phenylpropionic acid synthesis question
« Reply #2 on: December 06, 2009, 10:10:55 AM »
Al/Hg?

shroomedalice

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Re: Phenylpropionic acid synthesis question
« Reply #3 on: December 06, 2009, 10:34:23 AM »
nope wont work.

though if the new method of reduction works ie with the ammonia nitrate and lithium in ether this will do the
job as it is a birch reduction.


« Last Edit: December 06, 2009, 02:00:25 PM by shroomedalice »

no1uno

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Re: Phenylpropionic acid synthesis question
« Reply #4 on: December 06, 2009, 11:04:43 AM »
This, look around, see if the Urushibara/other precipitated Nickel catalysts would work instead, otherwise go get yourself some catalytic converters (must see if I can find all the papers I had on those suckers >:(, from memory they used Chlorates to oxidise/dissolve the metals of interest and then a resin to separate them). Here is another using Pd/C, although the STP hydrogenation (under a balloon) might be preferable in your situation... Here is one more (the one I was thinking about actually), but you'll note in the comments "bullshit" has been called... Waiting to see a "REAL" response. ::)
« Last Edit: December 06, 2009, 11:08:38 AM by no1uno »
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Wizard X

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Re: Phenylpropionic acid synthesis question
« Reply #5 on: December 06, 2009, 11:30:37 AM »
Quote from: heisenberg on December 06, 2009, 01:52:53 AM
I am looking into the easiest methods to synthesize phenylpropionic acid. The probable starting material would be a benzaldehyde, which would then be used to form a cinnamic acid. The tricky part is the reduction of the cinnamic acid using OTC materials.
If a solid and easy synthesis could be found, it would open up the ability to make various substituted indanes (2-aminoindane, MDAI, jimscaline, etc.). Phenylpropionic acids can be readily cyclized to form 1-indanones, which to me look like a very good starting point for aminoindanes. It is also possible to cyclize phenylalanine derivatives into 2-amino-1-indanones using a similar method, although the nitrogen must be protected. I will post the articles supporting this once I finish purging them of metadata.

Aminoindanes are quite legal so far, and the series has not been completely explored by human test subjects. Only a few in the series have been bioasseyed, with varying results. In any case, I believe they show great promise as possible "drugs of tomorrow".

So, I ask the question: what do you guys think is the best/easiest way to reduce a cinnamic acid to a propionic acid?



Cinnamic acid ==[electrochemical reduction with Hg electrode]==> HYDROCINNAMIC ACID ( Phenylpropionic acids) http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0311
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."

heisenberg

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Re: Phenylpropionic acid synthesis question
« Reply #6 on: December 06, 2009, 04:09:08 PM »
Quote from: Wizard X on December 06, 2009, 11:30:37 AM
Cinnamic acid ==[electrochemical reduction with Hg electrode]==> HYDROCINNAMIC ACID ( Phenylpropionic acids) http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0311

Thanks, that looks very doable.

I've attached three articles, two about the cyclization and one about the synthesis of a large amount of DOM indane analogs.
I spent all my money on booze and hookers, the rest I wasted - Charles Bukowski

Baba_McKensey

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Re: Phenylpropionic acid synthesis question
« Reply #7 on: December 06, 2009, 06:44:01 PM »
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