Mescaline via Catalytic Hydrogenation

Mescaline via Catalytic Hydrogenation by KrZ

3,4,5-trimethoxynitrostyrene

Place the following in a 2L RBF;

• 250g 3,4,5-Trimethoxybenzaldehyde
• 500ml Nitromethane
• 10g Ammonium Acetate (anhydrous)

Procedure

• Gently reflux for 5-6 hours
• Cool and distill off any residual nitromethane.
   

  If the crystaline mass prevents distillation, remove it by vacuum filtration and use what is collected OR distill off the filtered nitromethane solution to collect an additional crop of crystals (If the crystals are stuck in the flask skip to the next step).

• Add enough boiling MeOH to dissolve the entire mass (If it’s stuck in the flask, if not skip this step, filter, and recrystalize once from boiling MeOH)
• Decant, cool and vacuum filter, repeat the recrystalization if the crystals are not a pure yellow color (which they usually are).

Hydrogenation

• 15g Pd/C 5%
• 175g 3,4,5TMBnitrostyrene
• 2.5L Anhydrous EtOH
• 100ml 31.45% HCl

Procedure

• Add reagents to the keg, begin vigorous stirring
• Remove atmosphere and pressurize to 75psi with H2
• React for 8-10 hours or until H2 uptake has completely ceased
• Evacuate H2 outside, vacuum out interior of vessel, allow H2 to clear, THEN open the vessel
• Vacuum filter off Pd/C
• Re-filter through celite for maximum Pd/C recovery/removal
• Distill the mixture down until the Ethanol fraction begins to cease
  • Cool and take up what is left in 2L 3N HCl
     

    Your remainder may look somewhat black/brown here, but don’t worry, this will all be cleared up. If the hydrogenation did not go to completion some unreacted nitrostyrene will remain, this should be filtered from the solution.

• Wash with 2x125ml DCM
• Basify to pH>11 dropwise and with stirring with saturated NaOH solution
• Extract 3x125ml DCM
• Dry over NaSO4 (250g) for 15 minutes
• Filter off NaSO4 and bubble DCM with HCl(g) anhydrous. After crystalization ceases it can be advantageous to filter and redry the DCM with another 100g NaSO4, then bubble some more.
• Collect HCl salt crystals by filtration

Final mass yield = 168.74g Mescaline•HCl

Addendum:Prisoner 655321. Into a Ghetto Reactor ™ there was placed 890g 3,4,5-MeO-nitrostyrene (you know which one), this was dissolved in EtOH (2l), and 80ml of from the bottle concrete cleaner was added (31.45%), then 25g of 3% Pt/C was added and the reactor was stirred vigorously. The reaction was cooled in an ice bath. Atmosphere was removed and 80psi of H2 was added. Pressure was supplied as needed and when the reaction was complete (6hrs), it was filtered through celite, washed with DCM, and then basified with aq. ammonia (500ml), it was then extracted with 4 200ml portions of DCM. The DCM was bubbled with HCl gas to produce, 588.54g of Mescaline Hydrochloride.