Not very familiar with this rxn so dont take this as specific advise or my word as gospel, but it strikes me as odd to have the workup start with brine and end with NaOH. Usually the rationale of a workup is
i) deactivate the reagent (presumably the purpose of the NaOH??)
ii) extract/remove the reagent (presumably the intention of using aqueous washes)
iii) remove anything left from steps (i) and (ii), usually water/salt/acids/bases (in most cases, finishing with a DI water/Brine combination wash…maybe some HCl+Bicarb to remove NaOH, etc)
Sometimes steps (i) and (ii) are a single step, like adding aqueous base (bicarb, sodium hydroxide, etc) to an organic reaction with an acid catalyst (pTSA, HCl) - the base deactivates the acid by turning it into a salt, and the water extracts the salt all in a single step. And then from there you try and remove leftover base/salt/water (step iii) with HCL/Bicarb/Brine. This is a very general example, there’s a lot of nuance I’m glossing over.
Sometimes steps (i) and (ii) are separate because the method of extraction is incompatible (hazardous) with the active form of the reagent. Like if you’re using a reagent that reacts violently with water, but extracts well into water - you might hit it with alcohol/DCM to kill reactivity, and then extract into water in two separate steps. Again, just a general example.
I think you should assess what each step in your workup is supposed to be doing and whether or not its actually achieving its intention, and whether the order of operations makes sense in that context. In your workup, I don’t know if citric acid is even doing anything - and even if it is, I suspect that there are better options.
If your last wash is a strong base, you PROBABLY want some washes after that which remove the strong base. Cannabinoids go purple around bases, sometimes irreversibly. Theres a chance that if you adjusted your final pH back to like 5-7 you’d see that purple go away. But also yes, if you left unreacted CBD in there then you probably have done some damage by hitting it with base - monitor your rxns with HPLC, GC or TLC before quenching.
If I was using NaOH to quench something, I’d follow it with some acid/water to pull out the NaOH, and maybe follow that with bicarb depending on what acid I used, and then follow that with water/brine to get rid of any lingering bicarb/water/salts. DCM is a bitch for aq workups, you may need to swap for the workup.