mda is easy to crystallize if it's pure, i found it easier to work with than mdma.
i think this is because mda does'nt form hydrates like mdma does.
hey i just got  idea!!!  mix mandy powder in pixie sticks candies, the kids they would just love that!!!
'mandy candy! it's so swell, it makes you dandy!'

I now know how to run a GC/MS and going to learn H NMR next week, so I’ll eventually plan to run some MDA or MDMA to see what kind of impurity is present  depending on how the workup is done. That could be of interest to bees/wasps on this site as far as I know

that would be the amazing, i've always wondered.  jon recommended using anhydrous EtOH as a recrystallization solvent for mda.  i ended up with pinkish mda that was in desperate need of washes and recrystallization.  after the washes and EtOH recrystallization they were clusters of little colorless glass needles that crushed into a very crystalline white powder.

As for refluxing, how can you not reflux?? Only way I see it would be possible would be by running the reaction in an ice bath...Otherwise the reaction content reflux by itself...I’ve never added external heating.

on no you definitely need to reflux during the reaction, sorry for the bad wording.  i meant the refluxing for a few hours after the reaction.  the external heating is nice for small scale al/hg's because it kicks off the amalgam really fast.  i used external heating out of habit but for this reaction i wouldn't recommend it b/c you there is no addition rate, you just toss everything in when the amalgamation occurs.  unlike small scale nitro al/hg's where timing is much more important.

For MDA recrystallization in anhydrous  IPA seems to do the trick from what I hear. I have heard good things about triple rxing it in  anhydrous EtOH

Solubility issues. It is much more soluble in MeOH, making effective recrystallization difficult.

so i prepared a small batch of oxime.  i washed it with 10% AcOH and it didn't seem to help it when it came to the oxime drying faster.  seemed to dry about the same rate, it took 2 days.  maybe it dried a little faster.  next time i'll wash it with 10% AcOH again followed by one single light wash with freezer cold MeOH.  this is in hopes that it will remove unreacted oils to allow it to dry faster.  i'm pretty sure that the oxime takes so long to dry because of the presence of a small amount of isosafrole keeping it a little wet.

then i proceeded to waste 4g of oxime.  i should've paid better attention, anyone add the oxime too soon and kill the amalgamation before it had the chance to pick up steam?  probably not, but i'm here to confirm that it can happen...

ambient temp: 58F
0:00
charged a 500ml RBF with a stirbar, 70g MeOH, 18.5h H2O.  stoppered the flask and turned stirring on to dissolve the hgcl2.  left to go run errands
5:00
attached a reflux condenser fed with cold water, added 6.6g Al.  turned off stirring and did 10 second stirbursts every 1 minute instead.
5:10
the MeOH is a little murky but the al is still shiny
5:20
the al is a little dull but that's all.  amalgamation isn't ready yet
5:24
a couple h2 bubbles were noticed but it's not a steady pace, there were only a few every couple of minutes.  still not ready yet.
5:26
a couple more h2 bubbles are noticed, went ahead and added 4g oxime & 14.6g AcOH
5:28
no change, bubbles have stopped.  the solution went a little darker upon addition of the oxime and AcOH.  the oxime was added too soon and the amalgamation wasn't ready yet.  the addition of oxime and AcOH is now preventing the amalgam from forming properly.... fuck
6:00
added 90mg more hgcl2 and turned stirring on in hopes it will amalgamate
7:00
nope, nada.  what a waste because i was jumpy with the addition, should've waited another 5-10 minutes.  i'm in a habit of using external heat which kicks off the amalgam almost instantaneously and decided to not use external heat for a change.  damn it.  the last amalgamation i did before this one was a MM nitro al/hg and the amalgamation picked up its pace a bit faster, but then the ambient temp was 10 degrees warmer then as well.

good idea.  i gravity filtered the solution to remove the al foil, then washed the filter cake of unreacted al foil with fresh MeOH.  there was no oxime in the filter so it must be dissolved in the gray MeOH along with the small portion of glacial acetic acid in there.  so i prepared a new al/hg and had the gray MeOH/oxime/AcOH solution in an addition funnel.  waited 35 minutes until the amalgam had a few large pieces of al foil floating, most of the al was dull, and there were constant bubbles.  i started the drip-rate at a slow stream and stopped periodically, the h2 bubbles continued evolving from the amalgam so i continued drip-rate.  unfortunately the amalgam slowly died upon addition of this solution... WTF al/hg's are so picky.

next time i'll go back using external heat to preheat the MeOH + HgCl2 solution.  then when the solution reaches 55-65C i add the al foil and it amalgamates instantly or within 1-2 minutes.  i do nitro al/hg's without external heat with no problem but with this one i can't seem to get the hang of it without external heat.  but adding AcOH too early appears to kill the amalgam.  i'm surprised it killed the reaction because the amalgam was clearing going, any nitro al/hg starting the addition too soon will cause problems because when it eventually reacts it could all react at one time and end up sending the reaction into overdrive.  with this one, the AcOH addition kills the amalgamation.  i fucked up not once but twice, so back to external heat i guess.

AB2, what is that sludge that forms whenever I form the oxime?  Any suggestions on how to deal with that mess?

antibody i could'nt remember reactions i did that long ago with that kind of detail.
you have excellent recall.
one question, acetic acid is just a co-solvent correct?

yeah i was wondering about that it would suggest nascent hydrogen and not overvoltage as the mechanism.
in which case all you would need is a dissolving metal reduction.

Hi Neil
Thanks for the props, you've got a good memory! Yes, performic RXNs were used to form the ketone in all instances

The problem with MMDA was that the myristicin was a very small fraction distilled from oil of parsley. During the initial fractional distillation there were NO solid fractions, the thermometer was on the move the entire time, by the time the blurry fraction that was assumed to myristicin was isomerized, put through a performic RXN, the batch was too small to distill with a 24/40 rig, so it was purified via bisulfite adduct, hydrolysed and then onto oximation. The product was the red syrup reffered to a couple posts above. So to say the yield was 10% is misleading, the precursers were not very pure, so it is hard to say what the yield actually was.

However the apiole fraction from that same run was much larger >> easier to purify >> better yield>> and the DMMDA was absolutely sublime and more than worth all the effort.

with DMMDA2, in hind sight working from dill apiole which is readlily available in almost pure form, AB2 doesn't think the oximation or reduction failed. The failure in hindsight was in forming the salt. After passing dry HCl through the post rxn extraction, the product was a honey coloured oil, which was assumed to be a failure, and discarded without bio assay (MISTAKE!!!) subsequent trials crystalizing using dilute H2SO4 formed salts every time, although with some decomposition. So from that perspective the preceeding rxns were successful, AB2 just didn't realize it at the time and threw the baby out with the bathwater. sigh.

DMMDA2 is difficult to form acid salts with. If that RXN were run again, AB2 would use fumaric acid to form the salt instead.