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reaction mechanism, synthesis of salicylic acid from methyl salicylate, NaOH and H2SO4

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.55P: Several diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show...

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reaction mechanism, synthesis of salicylic acid from methyl salicylate, NaOH and H2SO4

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1) Hydrolysis of Methyl Salicylate: Methyl Salicylate (C8H8O3) + sodium Hydroxide (NaOH) -> sodium Salicylate ( NaC7H5O3) + Methanol (CH3OH) 2) Acidification of Sodium Salicylate: Sodium salicylate (NaC7H5O3) + HCL -> Salicylic acid (C7H603) + sodium chloride (NaCL) Could you find the theoretical yield for me? 2.15g of methyl salicylate was used. 25ml of sodium hydroxide (2m solution) was used for hydrolysis and 2ml of hydrochloric acid was used for the acidification. This produced a yield of 1.53g of salicylic acid.
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