Oil of Wintergreen: Preparation of Methyl Salicylate
CHEMISTRY 203:Organic Chemistry II
The purpose of this experiment was to determine if reacting an acid with an alcohol produced an ester. In this experiment the carboxylic acid of acetylsalicylic acid was esterified by methanol and produced methyl salicylate (oil of wintergreen).1 Thin layer chromatography and infrared spectroscopy were utilized in determining that the liquid collected was in fact an ester.
An ester is an organic compound formed through the process of esterification, which involves the reaction of an alcohol and an organic acid. Esters are common derivatives of carboxylic acids and also constitute an important functional group family of their own. Esters are produced on a large scale commercially, as they are known for their flavoring and fragrance of many fruits, flowers, artificial flavors, and perfumes. Esters are responsible for the sweet taste and smell of common items such as bananas, oranges, pineapples, apples, and rum. Esters are also used commercially as solvents, plasticizers, starting materials for polymers, as well was pharmaceuticals.1
Methyl salicylate, otherwise known as oil of wintergreen, is an ester with a characteristic wintergreen aroma. Oil of wintergreen was originally produced naturally from the wintergreen plant and Black Birch. Now oil of wintergreen is synthetically produced for medical purposes and used for flavoring teas, which aids in soothing muscles, headaches, and other pains. Oil of wintergreen can only be consumed in very small amounts in products, as it is a volatile and toxic substance, requiring only 6mL to kill an adult human.
In this lab, methyl salicylate was prepared from previously synthesized aspirin. The organic acid used in the esterification was acetylsalicylic acid and was reacted with methanol, an alcohol. A mixture of refluxing, separation, and rotary evaporation techniques were utilized in this lab to...
References: 1. Hill, Richard, and Barbaro, John. Experiments in Organic Chemistry. 3rd ed. Raleigh:
Contemporary, 2005. Print.
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