Salicylic Acid from Methyl Salicylate

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The synthesis of salicylic acid from methyl salicylate involves adding NaOH to methyl salicylate, heating the solution, and then adding HCl after cooling. The reaction produces sodium salts and water, but the exact composition of the filtrate after adding HCl is uncertain. It is believed that Na+ and Cl- ions are present in the filtrate, as they do not remain in the final product, salicylic acid. The reaction of HCl with sodium methoxide is unclear, leading to confusion about additional components in the filtrate. Clarification on the products formed during the reaction with HCl is needed for a complete understanding of the filtrate composition.
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Homework Statement


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?

Homework 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.

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!
 
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You don't have sodium methoxide in water.
 
Oh, okay, so I just have big benzene ring with the sodium and water. But what about the filtrate?
 
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