Synthesis of Aspirin
Jennie K. Daniels
Organic Chemistry 2121
11 February 2014
Synthesis of Aspirin
Salicylic acid derivatives, or salicin, are found in the bark of the willow tree. In the 5th century B.C., Hippocrates ground the bark into a powder, and later, the Natives Americans chewed on the bark to alleviate fever and pain1. In the 19th century, a German chemist by the name of Felix Hoffman wanted to find a medication that would ease his father’s arthritis without causing irritation to his stomach. The standard arthritis medication at the time, sodium salicylate, could not be tolerated by many patients, Hoffman’s father included, due to the irritation of the stomach lining brought and by large doses 2, Hoffman synthesized acetylsalicylic acid ‘through some chemical reactions that covered up the acidic portions with an acetyl group’ 3, and was found to alleviate fever, minor pain, and arthritis pain at higher doses. In 1899, the Bayer company sold aspirin for the first time commercially in Germany and in the United States in 1900 4. In recent years, it has been proven that aspirin helps prevent heart attacks in patients with heart disease and in healthy men over the age of 50. To prevent a heart attack, low dose aspirin (81-325mg) is used. During a heart attack, a 325mg, non-coated aspirin tablet must be chewed to prevent blood platelets from clotting. The tablet must be uncoated due to the aspirin acting slow, and the tablet must be chewed because the healing reactions are fastest with this method (14 minutes chewed vs. 26 minutes swallowed) 5. Reaction Scheme
Mechanism
The purpose of synthesizing aspirin, other than to find a less intestinal irritating pain reliever is to determine if the experiment will work using current methodology and to determine the resulting compound’s purity by obtaining the melting point 6. Aspirin is a common medication for reducing fever, aches, and pains.
Organic Chemistry 2121
11 February 2014
Synthesis of Aspirin
Salicylic acid derivatives, or salicin, are found in the bark of the willow tree. In the 5th century B.C., Hippocrates ground the bark into a powder, and later, the Natives Americans chewed on the bark to alleviate fever and pain1. In the 19th century, a German chemist by the name of Felix Hoffman wanted to find a medication that would ease his father’s arthritis without causing irritation to his stomach. The standard arthritis medication at the time, sodium salicylate, could not be tolerated by many patients, Hoffman’s father included, due to the irritation of the stomach lining brought and by large doses 2, Hoffman synthesized acetylsalicylic acid ‘through some chemical reactions that covered up the acidic portions with an acetyl group’ 3, and was found to alleviate fever, minor pain, and arthritis pain at higher doses. In 1899, the Bayer company sold aspirin for the first time commercially in Germany and in the United States in 1900 4. In recent years, it has been proven that aspirin helps prevent heart attacks in patients with heart disease and in healthy men over the age of 50. To prevent a heart attack, low dose aspirin (81-325mg) is used. During a heart attack, a 325mg, non-coated aspirin tablet must be chewed to prevent blood platelets from clotting. The tablet must be uncoated due to the aspirin acting slow, and the tablet must be chewed because the healing reactions are fastest with this method (14 minutes chewed vs. 26 minutes swallowed) 5. Reaction Scheme
Mechanism
The purpose of synthesizing aspirin, other than to find a less intestinal irritating pain reliever is to determine if the experiment will work using current methodology and to determine the resulting compound’s purity by obtaining the melting point 6. Aspirin is a common medication for reducing fever, aches, and pains.