So I recently dreamed of an extraction where 3 pounds of acacia confusa trunk bark was soaked for 2 days in acidic distilled water then boiled 4 times for about 45 min each and all the water was collected and boiled down. based with naoh and pulled with naphtha. yielded about around .8%. anyways i wasn't able to boil the bark as many times as i wanted due to time restrictions so i expected the bark to have quite a bit left especially considering it wasn't quite powdered more like well shredded with some larger shreds.

I soaked the bark in 70% iso and vinegar and soaked for a week and decanted off and resoaked the bark in about 2/3 70% iso, and 2/3 winegar mixed with water to top it off. the first alcohol soak came out very dark so i'm expecting a fair amount more.

in the past i evaped all the alcohol down until it didn't smell anymore and would add water then base whenever i would soak in isopropyl. I can't boil it off right now though because my roomate would get pissed.

Would i be able to basify a roughly 50% isopropyl-50% water solution and then pull with the naphtha? i know the naphtha creates a distinct layer with diluted isopropyl but i'm not sure if it completely separates or if some is still miscible with the alcohol. I wouldn't want any base mixture miscible in my naphtha or vice versa.

should i just wait until i can evaporate all the iso out to be safe?

afaik isopropyl is miscible with naphtha

Well that's assuming it's pure idk. My point is that I have seen a 70 percent iso to 30 percent water separate fairly well so I was wondering if it would be a problem if say maybe 10 percent iso remains from an incomplete evap.

I ask the informed of which chemical is best choice as a base: a. (C6H10O3) or b. (C4H11N)? One is tert-Butylamine and the other is Ethyl Acetoacetate. Both have pka ~ 10.68; 8.68 happens to be the pka of N,N Dimethytryptamine, and SWIM read once that within 2 range of the compound will convert 99%, thus 2 higher is ionized from the base: only the Nitrogen and the Oxygen attract my attention as different because I'm uneducated besides narrowing to those pka's...
Thanks!

the nonpolars don't typically mix with cationic/anionic solutions, except those that are miscible with water. Ethyl acetate, acetone, and ethyl ether would be somewhat miscible, and dcm would be miscible.

Doing that with a basified 50/50 iso/water mix would be messy.
If you were to toss a fist full (enough to saturate the water) of rock salt in and repeatedly stir it over 1-2 days the saltwater and iso will separate well, with most of the base, crap, and salt in the water, and most the alks (and a bit of base and salt and crap) will be in the iso layer. The iso would then be easier to evap until naphtha and then water could be stirred in for cleaner separation.

Conversely, you could salt it while its still acidic, then wash the iso layer with fresh salt water, combine salt waters, base that and use naphtha on that. The waste iso might be useful for something.
Not sure how much of the alks would stay in the iso as the acetate tho.