Today in lab we synthesized acetylsalicylic acid (aspirin) by combining salicylic acid and acetic anhydride. To purify our product from any unreacted salicylic acid and the byproduct acetic acid, we used recrystallization with a 95% ethanol-water solution. How was this able to work? Ethanol and water are both quite polar, and acetylsalicylic acid has more hydrogen bond-accepting groups than the other two molecules, so shouldn't it have been more soluble in the solution than them? My only guess is that ethanol is 2/3 nonpolar, so it has less of an affinity for aspirin than it does for salicylic acid and acetic acid, but I didn't think this would matter as much due to the strength of hydrogen bonds.