Salicylic Acid from Methyl Salicylate

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SUMMARY

The synthesis of salicylic acid from methyl salicylate involves a three-step process: adding NaOH to methyl salicylate, heating the solution, and then adding HCl after cooling. The reaction produces sodium methoxide (NaOMe) and water (H2O) upon the addition of NaOH. The filtrate after filtering the product contains Na+ and Cl- ions, as well as residual water, but does not include salicylic acid, which is the final product of the reaction.

PREREQUISITES
  • Understanding of organic chemistry reactions, specifically ester hydrolysis
  • Familiarity with the properties of sodium hydroxide (NaOH) and hydrochloric acid (HCl)
  • Knowledge of filtration techniques in laboratory settings
  • Basic grasp of ionic compounds and their behavior in solution
NEXT STEPS
  • Research the mechanism of ester hydrolysis in organic chemistry
  • Study the properties and reactions of sodium methoxide (NaOMe)
  • Learn about the role of acids in neutralization reactions
  • Explore advanced filtration techniques and their applications in organic synthesis
USEFUL FOR

Chemistry students, organic chemists, and laboratory technicians involved in synthesis and purification processes will benefit from this discussion.

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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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