Experiment four: Synthesis of Salicylic Acid from Wintergreen Oil Organic chemistry 331 Lab of 10/8/13
Abstract: Methyl salicylate is used as a flavoring because of its pleasant penetrating odor. Methyl salicylate was heated under reflux with the addition of NAOH as a solvent and cooling the mixture with H2SO4. Then the product was purified and the mass of the product weighed 2.6914g and the melting points of the purified product ranged from 141-145 degrees C and the mixed product (salicylic acid + purified product) ranged from 150=160 degrees C.

Introduction For many years, commercial methyl salicylate was obtained from wintergreen oil, an aromatic liquid distilled from the leaves of the wintergreen plant. There is no difference between the pure natural and synthetic forms of methyl salicylate because they are both composed of the same kind of molecules and must have the same properties. Medicinally, wintergreen oil has some the painkilling properties of salicylates, which are a group of organic compounds that include salicylic acid and aspirin. Lehman (2002) The purpose of this lab is to determine whether salicylic acid from methyl salicylate is no different from salicylic acid made from benzene. The strategy of this lab was the preparation of salicylic acid from methyl salicylate using an apparatus for heating under reflux. Materials & Methods Methyl salicylate, 1.261ml followed by a 15ml of 6M sodium hydroxide and 2 boiling chips were measured into a boiling flask and the reaction was heated under reflux for 30 minutes, from the time it started boiling. The reaction was transferred to a beaker, and 16mL of aqueous 3 M sulfuric acid was slowly added to the reaction to test the pH of the supernatant liquid to have a pH of 2 and then the mixture was cooled in an ice bath for 10 minutes. The product was collected by vacuum filtration and the filtrate was