Synthesis of Aspirin 4 - Aspirin Synthesis Your team of...

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Aspirin Synthesis Your team of scientists has been hired by the drug research division of Santa Monica Pharmaceuticals, a new start-up company formed by some SMC alumni. You have been asked to evaluate a simple organic synthesis for Aspirin and to determine if the synthesis merits further funding by Santa Monica Pharmaceuticals. You will have one week to test the synthesis, evaluate the purity of the product and make your recommendations. In many ways, the science of organic synthesis is like finding the solution to a puzzle. The goal of organic synthesis is always to prepare a target molecule, perhaps chosen because of its intrinsic scientific importance or, perhaps, because of its economic importance. The constraints imposed upon the synthesis are what makes it challenging to the synthetic chemist. For example, often a route is chosen because the starting materials and reagents are available inexpensively or in sufficient quantities. Often working against this constraint is the fact that, for efficiency, a synthetic route should involve the least number of steps possible, because each chemical and physical step reduces the overall efficiency. The choice of the most efficient route is also affected by other constraints. Sometimes (although not in this lab!), efficient synthetic routes involve highly reactive or toxic species, even if the product has none of those properties. Such a route might improve efficiency, but it would also increase the complexity of the synthesis because of the additional safety precautions that would need to be implemented. Finally, the end use of the product often dictates the acceptable level of purity of the material. Typically, chemicals destined for use as pharmaceuticals or in the electronics industry are needed in extremely pure form. Purification strategies can often be as complex as the syntheses themselves. In the first part of the lab your team will make aspirin, purify your product and calculate the percent yield. In the second part of the lab you will perform quality control experiments on your aspirin, similar to the kinds of tests that are required by the FDA. C O CH 3 O C OH O H H H H Figure 1 Acetylsalicylic acid (aspirin), C 9 H 8 O 4 Aspirin (acetylsalicylic acid) is a versatile drug that is consumed in huge quantities worldwide. It is a non-steroidal anti-inflammatory drug (NSAID) with a wide range of physiological effects. At very low doses, aspirin is used to treat and prevent heart attacks and blood clots. At higher doses
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it is used as an analgesic to reduce pain and as an antipyretic to reduce fever. At very high doses, it is an effective anti-inflammatory agent used to treat rheumatic fever, gout and rheumatoid arthritis. It is also an anticoagulant, it dissolves corns and calluses, and it provokes loss of uric acid (a toxin) but promotes retention of fluids in the kidneys. It kills bacteria and induces peptic
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This note was uploaded on 04/23/2010 for the course CHEM CHEM2220 taught by Professor Andreana during the Fall '10 term at Wayne State University.

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Synthesis of Aspirin 4 - Aspirin Synthesis Your team of...

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