HMA Synthesis by sandymouseguy
Reaction 1:
https://imagebin.ca/v/3wO95yfmkVq9
Reaction 2:
https://imagebin.ca/v/3wO9GHTGir41
Reaction 1 Reagents:
Vanillin 30g, 0.197109mol, mw = 152.2 g/mol
Ammonium Acetate 12g, 0.155642mol, mw = 77.1 g/mol
Nitroethane 21g, 0.279627mol, mw = 75.1 g/mol
Reaction 1 Procedure:
Add 21g of nitroethane, 30g of vanillin, 12g anhydrous ammonium acetate, 63g of glacial acetic acid to a 1L round bottom flask (RBF). Begin stirring with a magnetic stirrer and keep covered until dissolved. Next begin refluxing gently but keep it from boiling. Reflux until a red color begins to form. Once this red color begins to form immediately remove from heat (Red is a sign of impurities forming). Flash cool the reaction mixture by dumping it into a beaker of ice. The product will begin to crystallize. Wash the reaction flask with some distilled water and add it to the ice beaker. Let the ice melt and the solids settle. Vacuum filter the product. Recrystallize the product with a 60:40 methanol:water solution. Vacuum filter the recrystallized solids and wash them with ice cold distilled water. Store product in freezer. Keep away from water and the product should be used within a few days in the next step because it is quite unstable.

Reaction 2 Reagents:
Vanillin 2-nitropropene 15g, 0.071702mol, mw = 209.2 g/mol
Aluminum Powder/shreds 13.49g, 0.5mol, mw = 26.98 g/mol
Urushibara Catalyst 29.35g, 0.5mol, mw = 58.693 g/mol[1]



Reaction 2 Procedure:
Dissolve 15 g of Vanillin 2-nitropropene in 80 ml of ethanol in a RBF. Add 29.35g of Urushibara Catalyst. Use constant mechanical stirring.[2] Add 1g of aluminum and drop in conc. HCl until the Al is dissolved. Continue this by adding 1g intervals of Al the  adding HCl until all Al is used up.[3] After Al & HCl addition, add 7.5M NaOH solution until all acid is neutralized. Decant into separation funnel and allow to seperate. Drain out bottom aluminum layer and discard. Dissolve the remaining orange layer in acetone in a beaker. Drop in sulfuric acid gently to precipitate the the product sulfate salt. Recrystallize in acetone after vacuum filtering.

Footnotes:
[1] - Urushibara Catalyst is a porous nickel catalyst. There are write-ups on rhodium and videos on youtube (ChemPlayer) on how to prepare this.
[2] - Use overhead mechanical stirring as a magnetic stir bar will magnetize the nickel and cause it to clump.
[3] - The Al & HCl addition intervals may take 4-6 hours.
[4] - I recommend listening to Death Grips while synthesizing your product