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Salicylic Acid from Methyl Salicylate

  1. Sep 19, 2011 #1
    1. The problem statement, all variables and given/known data
    In a lab, we are synthesizing salicylic acid fro methyl salicylate. The following steps are used:
    1) Add NaOH to Methyl Salicylate
    2) Heat solution
    3) When solution has cooled, add HCl, then filter product

    My question is, what is present in the filtrate when filtering the product?

    2. Relevant equations
    When adding NaOH, we get:
    methyl salicylate (but with Na's attached to the Oxygens), NaOMe, and 2H2O

    When adding HCl, I'm not certain what results.

    3. The attempt at a solution
    I believe that Na+ and Cl- are in the filtrate, because surely those atoms are not in the final product (salicylic acid). But, I'm not certain what else is in the filtrate. For instance, when HCl is added to NaOMe, I'm not sure what the product is. Any help is much appreciated!
  2. jcsd
  3. Sep 19, 2011 #2


    User Avatar

    Staff: Mentor

    You don't have sodium methoxide in water.
  4. Sep 19, 2011 #3
    Oh, okay, so I just have big benzene ring with the sodium and water. But what about the filtrate?
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