Separation of solid mixture by extraction

[jnimagine]

Hi,
I have a question about separation of solid mixture by extraction.
so how can you tell what reacts with what and which layer contains what?
k for example, if you have a mixture of phenol and salicylic acid, first the mixture is dissolved in diethyl ether... then the solution is mixed with sodium bicarbonate. What does aqueous and ether layer contain?

 

[symbolipoint]

Not sure if phenol acts like an acid or a base; but salicylic acid can be neutralized so then its salt would not be soluble in diethyl ether. Someone else, who knows the acid/base chemistry of phenol would have to give further remarks about this.

 

[Borek]

Phenol is weakly acidic with pKa 9.9, while salicylic acid has (first) pKa 3.0. What is pH of the sodium bicarbonate solution? What fraction of phenol will be ionized at this pH? And of salicylic acid?