[Mr.rose]

Thankyou for your information, but I have one problem, when i puleld that info, it said the solubility of estrodial is 2.5mg/L in ethanol, it never mentioned estrodial benzoate, which is why i believe the solubility will much different. And for the life of me i cannot find its solubility in actual units.

One abstract i found for Testosterone propionate is:

This product is soluble in chloroform (50 mg/ml). It is
also soluble in a number of oils, including ethyl oleate.7
The oil solutions can be sterilized by maintaining at
150 °C for 1 hour. It is practically insoluble in water,
soluble 1 in 6 of ethanol, 1 in 4 of acetone, 1 in 20 of
ethyl oleate, and 1 in 30 of propylene glycol.

But i do not know what units they are referring to when they say "1 in 6" etc.

[democanarchis]

1 in 6 I would take to mean 1mg/6mL. In that case, and given all the confilicting solubility data i'd pick the recrystallisation method. You won't get greater than 90% yield but it should be completely pure - you will only get one product crystallising. When you dry it then recrystallise again, verify which chemical the filtered solid is, as the minor product may crystallise given the change in product ratio, but again, it should be pure. 2 crystallisations should give you >95% yield pure.

You mentioned ethanol as a solvent for recrystallisation - as one of your materials is nearly freely soluble in it, its a bad choice. I'd try the hexane first, then maybe something a bit more polar like toluene if that doesnt work