guaguanco
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alternate mescaline synthesis
I wished I had tried this back when I had my lab, since I actually had a small jar of 3,4,5 trimethoxybenzaldehyde and the other required reagents:
ArCHO + Ac2O/NaOAc -> Ar-CH:CH-COOH
ArCH:CH-COOH + NaBH4 -> Ar-CH2CH2COOH
Ar-CH2CH2COOH + NaN3/H2SO4 -> Ar-CH2CH2NH2
All steps are (or should be) high yield.
I've never seen this pathway discussed in the preparation of phenethylamines, and Shulgin could do a LiAlH4 reduction in his sleep, so he
didn't need it.
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ziqquratu
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At first glance, and I may be wrong, but wouldn't the sodium borohydride preferentially reduce the carboxyl group? I dont have time nor
inclination to check out (or try to remember) any of your other steps, so I don't know if they'd work...
Irrespective, you'd probably have better luck finding this at the Hive.
[Edited on 13-12-2003 by ziqquratu]
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unionised
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It might not be the end of the world if it did preferentially reduce the carboxylic acid group. I'm fairly sure that you could turn the acid into
an unsaturated ester, reduce that to the saturated alcohol with NaBH4 then oxidise it back to the saturated substituted propanoic acid.
A bit clumsy, but it might work.
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guaguanco
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Actually, carboxylic acids are surprising resistant to reduction. You'd have to first convert it to tha acid chloride if you wanted to cleanly
reduce it to the aldehyde.
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unionised
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Who mentioned the aldehyde?
Anyway, isolated double bonds are suprisingly resistant to reduction by NaBH4. Conjugated ones are a whole lot easier, but they can't be
conjugated to a free acid, or it doesn't work.
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guaguanco
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| Quote: | Originally posted by unionised
Who mentioned the aldehyde?
Anyway, isolated double bonds are suprisingly resistant to reduction by NaBH4. Conjugated ones are a whole lot easier, but they can't be
conjugated to a free acid, or it doesn't work. |
Well, it was implied in the previous posts...
Actually, I've found recipes for reduction of cinnamic acids to phenylpropionic acids on the web using NaBH4; another route would use catalytic
hydrogenation using formate as a convenient hydrogen donor.
Quite amazingly, I just looked in my little box of chemical mementos from the old days and found a 25 gm bottle of 3,4,5 trimethoxybenzaldehyde !! I
would never have believed I still had it.
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Organikum
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I remember a electrosynthesis for this compound - posted at ADC......
If interested I dig it up, but I believe it is on Rhodiums page already also I am not sure if the version there is complete.
I also fear the reduction of the COOH not being so easy as we would like it to be - as I have promised somebody to search my archives for the
carboxylic acid reduction I can post the results here.
So somebody cares.
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Darkfire
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Mescaline seems to be must cheaper and easyer just to grow than to make,
\"I love being alive and will be the best man I possibly can. I will take love wherever I find it and offer it to everyone who will take it. I
will seek knowledge from those wiser and teach those who wish to learn from me.\" Duane Allman
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unionised
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For some strange reason the chemical "Nitromethane" has sprung into my mind.
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guaguanco
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| Quote: | Originally posted by unionised
For some strange reason the chemical "Nitromethane" has sprung into my mind. |
I have gone through my fair share of nitromethane in the past, but those days are long gone!
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