What byproduct might have formed (think anhydride), and how might the addition of water helped convert this byproduct into the desired product?
The question is based on an experiment that first converted methhyl salicylate to salicylic acid and then converted the salicylic acid to acetylsalicylic acid (aspirin).
CH3 1. NaOH OH 2. H2SO Oil of Wintergreen (Methyl Salicylate) OH OH Salicylic Acid (Acetic Anhydride) HJC CH H PO OH CH Aspirin (Acetylsalicylic Acid)
