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Oil Of Wintergreen

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Oil Of Wintergreen
Synthesis of Aspirin from Oil of Wintergreen

Objectives: In this experiment, the Oil of Wintergreen is put into an Erlenmeyer flask containing sodium hydroxide to create sodium salicylate. The solution is then refluxed which means that the solution will be boiled in a base, then condensed in a condenser. This replaces the carbon on the ester at carbon 1, with an oxygen atom which will have an ionic bond with a sodium anion. This yields sodium salicylate which will be acidified in methanol (CH3OH) which will remove the sodium bonded to the oxygen, and switch it to a hydrogen atom bonded to the oxygen, making an alcohol group. This new product is salicylic acid. Acetic anhydride is added to the salicylic acid to add an acetyl group to carbon 2 which will create acetylsalicylic acid
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The solution then gets foggy/cloudy and white snowlike precipitate is floating within the solution. Heat is added along with a stir bar. The stir bar starts stirring at minute 7. It begins to dissolve the white powder as it spins. At minute 26 the solution becomes clear with barely any flakes left. Sulfuric acid is then added and white flakes are formed. More acid is added until the pH paper turns red. The round bottom is filled with white precipitate. The precipitate is put onto a hirsh funnel that uses vacuum filtration to isolate the precipitate. The product is then added to a beaker with D.I water and heated. It’s put through the hirsh funnel . 3.68 grams of salicylic acid is recovered. The melting point is tested to compare to a perfect sample. The melting point is 146C0. The product is dried and added to a beaker with D.I. water and 10mL of acetic anhydride and 20 drops of concentrated sulfuric acid. This product is chilled to produce crystals. Its then filtered using a hirsh filter using vacuum filtration. Recrystallized and filtered one last time. The product is now acetylsalicylic acid

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