mescaline by 1atm Hydrogenation

panky · Mon Jun 13, 2005 7:18 am

In the rhodium archive theres a method for the reduction of the nitrostyrene of (among other things) mescaline. Has anybody been successful with this? Does it scale well? (its on 400mg, yeilding about one hit) 2g? 4g?

anime · Mon Jun 13, 2005 8:14 am

panky · Mon Jun 13, 2005 8:51 am

ta.

the method stipulates 0degC. this obviously suggests something goes awry at rt. i cant figure out what tho. Normally i'd expect to hydrogenate to near quantitative yeild. I guess the obvious way to find out is to do it, but i wouldnt be too keen on ruining it. i guess thats science....

transistor child · gnome

Nitrostyrenes can easily be reduced at 1atm with Zn/HCl.
Not the highest yields but it works (around 60% depending on what nitrostyrene you're working with).

The procedure was up on Rhodium/The Hive but can't be found in any of the archives.

Star-light · Blacklight bulb

panky · Tue Jun 14, 2005 4:26 am

thanks for reminding me of the zinc proceedure...

I once did a thought experiment involving a two step hydrogenation / zn/hcl reduction and it worked a treat. i guess using the right conditions i could have just done 1 of those...

i might do a thought experiment involving the zinc method, im not keen on thinking about 1g Pd/C per 1g nitrostyrene...

anime · Tue Jun 14, 2005 5:56 am

panky · Tue Jun 14, 2005 10:01 am

For what its worth, in theory, 1g 3,4,5-trimethoxynitrostyrene, 20ml EtOH stirring on an ice bath, 5g Zn and 30ml conc HCl added over 1hr, stirred for 1 more hr. Filterd off small amnt of residual solids, made sure it was basic, extracted 2 x CHCl3, vapped it down, threw in some diluted H2SO4 vapped that down* threw in some EtOAc, white powder ppt out, filtered.

270mg (21%**) in 3hrs. pretty crap, but not bad for only 3hrs. Im really not keen on more hard-core reductions (lith-al etc), and this seems a pretty inocuous method.

*shit started to go black, so its possible some was lost there... then theres the stuff i, in theory, spilt. maybe taking it up in EtOAc, then dropping H2SO4 would have been the better option....

** this is assuming i, in theory, got the right stuff out.... you never know eh?

anime · Tue Jun 14, 2005 10:40 am

panky · Tue Jun 14, 2005 11:00 am

i'll check them out. i fucked up my %-age up there, so its a little better... but still only 270mgs Smile

not too worried about blowing myself up (well, i am, but i know what im doing), just prefer smaller set-ups, quicker, less work-up... i guess im just lazy...

Guest · Tue Jun 14, 2005 3:14 pm

I remember reading vogels along time ago, ad he swore by zn/hcl reductions,
He also swore by Fe/Hcl reductions,
Glad to see thoery turned into practical chemistry,

I am a nubee when it comes to these exotic nitro compounds,
Are we talking just a plain nitrostyrene, or is that just the basic name for a higher nitrostyrene,

If someone has time, would they like to pave the way for the synthesis of this nitro styrene,

A link will do,

syn

transistor child · gnome

The only pain in the ass is the addition of Zn and nitrostyrene, other than that it's just waiting (atleast 12h) then a pretty damn straight work-up (except for the ZnO which could be a problem). The great part is that no reagents are controlled or hard to get, anywhere, and it's all non poisonous/safe so it can be done almost everywhere. For mescaline the slightly lower yield may suck (12h will give you 60-65%), but for other nitrostyrenes like 2,5-dimethoxy etc where the final compounds are very potent it doesn't really matter in my opinion (if you're not producing commercially). Just use PURE powdered zinc, and do the addition SLOWLY keeping an eye on temperature.

synthetika: Should work for most substituted nitrostyrenes, but not for nitropropenes.

EDIT: Found the original article: http://www.erowid.org/archive/rhodium/chemistry/leminger.html

mk-1 · Tue Jun 14, 2005 4:54 pm

Dont really know what you mean Synthetika, but u mean what i think -
3,4,5-trimethoxynitrostyrene is the resulting product from condensation of 3,4,5-trimethoxybenzaldehyde with nitromethane.
[IMG] http://img134.echo.cx/my.php?image=tmns3zp.gif [/IMG]
It can be reduced in 3,4,5-trimethoxyphenethylamine (mescaline).
The precursor (the benzaldehyde),
[IMG] http://img102.echo.cx/my.php?image=tmba5ss.gif[/IMG]
can be made via several ways, either starting from the Syringaldehyde and methoxylationg the 4- position
[IMG] http://img102.echo.cx/my.php?image=syringe3ww.gif [/IMG]
or from gallic acid
[IMG] http://img102.echo.cx/my.php?image=gallic0dy.gif [/IMG]
methoxylating it to 3,4,5-trimethoxy gallic acid
[IMG] http://img102.echo.cx/my.php?image=tmbacid0ke.gif [/IMG]
and then reducing the acid to the benzaldehyde.

EDIT : Sorry for not being able to put the images right here, but rather to link to it. dont know what went wrong.

mind · Tue Jun 14, 2005 5:52 pm

edited for your viewing pleasure Smile

(see above post for original)
--------------

Dont really know what you mean Synthetika, but u mean what i think -
3,4,5-trimethoxynitrostyrene is the resulting product from condensation of 3,4,5-trimethoxybenzaldehyde with nitromethane.

It can be reduced in 3,4,5-trimethoxyphenethylamine (mescaline).
The precursor (the benzaldehyde),

can be made via several ways, either starting from the Syringaldehyde and methoxylationg the 4- position

or from gallic acid

methoxylating it to 3,4,5-trimethoxy gallic acid

and then reducing the acid to the benzaldehyde.

-------------

mk-1,you are linking to a webpage, not to the picture itself.

anime · Sat Jun 18, 2005 11:53 pm

Anyone know if NaBH4 can reduce the acid to the benzaldehyde? (and referrences if possible).
(Or oxidize to to an aldcohol)