So I know I'm kind of experimenting here but... Maybe someone can give me a hand...

My Procedure:

1) NaOH + Water
2) Add bark
3) Agitate + Wait an hour
4) Pull with hot toulene
5) Pull from toulene with citric acid saturated water.

Here things went mostly ok... The citric water got very orange-yellow tinted, while the toulene cleared. A strange oily-looking white precipitate also existed in the water layer.

6) Separate keeping water.

7) Add concentrated NaOH Water to the dmt citric water until precipitate forms.

Within 15 minutes of a few small additions the solution went a lighter orange and became VERY cloudy.

Put the solution in the fridge, similarly to the fumeric salt to freebase method... Its been ~10 hours. There is some settling of white sediment... But also there is a floating transparent yellow and a yellowy oil ring on the surface...

Originally the play was to filter, however an attempt to filter a few ml's shows that the yellow oil is gonna get all jammed in the filter.

At this point I'm not sure what is what, and what to do to fix the issue... Thought about re-pulling from the whole batch with naptha/toulene... Maybe wait a few days and pray it settles and it is decant-able?

Any opinions on what could be going on?

Use heptane or simialr to pull from the based citric water. i usually do this when using toulene/xylene after pulling the last from bark.

Actually to my surprise, after letting it sit for ~48 hours a very reasonable amount of large xtals has settled. Going to give it another 24 hours and monitor progress of precipitant development.