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.ziqquratu - 12-12-2003 at 20:25
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]unionised - 13-12-2003 at 03:47
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.guaguanco - 13-12-2003 at 12:58
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.unionised - 13-12-2003 at 16:16
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.guaguanco - 13-12-2003 at 18:18
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.Organikum - 14-12-2003 at 13:33
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.Darkfire - 14-12-2003 at 19:06
Mescaline seems to be must cheaper and easyer just to grow than to make,unionised - 15-12-2003 at 15:57
For some strange reason the chemical "Nitromethane" has sprung into my mind.guaguanco - 15-12-2003 at 15:59
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!
