Synthesis of 1-methoxy-2-indanone
Ex. 1
As chief scientific officer of Mark, Inc. R&D, I have the responsibility of reviewing proposed syntheses for new drugs that our company wishes to develop. Our president has identify 1-methoxy-2-indanone as a desired target, and two groups in our R&D department have proposed syntheses for this molecule. After mensurable evaluation, I have selected the synthesis from Research host A as the one most likely to achieve success.
Two steps in the proposal from Research Group B have problems that allow cause those steps, and hence the boilers suit synthesis, to fail. In step 1, the use of Br2 in the presence of FeBr3 will result in bromination of the aromatic ring to give 5-bromoindane or else than 1-bromoindane. Had Br2 in the presence of ultraviolet light been employed instead, the reply would likely have succeeded to give the desired 1-bromoindane. Each of the conterminous three steps from group B would give the verbalise product from the say reactant, although I do not pick up why group B would want to prepare indane-1,2-dione (the stated product from step 4). Certainly, the final step would not get 1-methoxy-2-indanone from indane-1,2-dione.
Lithium aluminum hydride is a powerful reducing agent, and two ketone groups would be reduced to alcohols to give 1,2-dihydroxyindane as the final product. Furthermore, the protic solving methanol is likely to react with LiAlH4 as well. All-in-all, step 5 would be a messy reaction.
I respectfully disagree with our president that 1-methoxy-2-indanone is a good candidate for synthesis. many another(prenominal) over-the-counter NSAIDs such as aspirin, ibuprofen, and naproxen contain carboxyl acid groups, and our target molecule does not. I strongly progress research group A to conduct a essential literature search prior to investing the time, effort, and material be needed to synthesize 1-methoxy-2-indanone. In addition, I...
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