Anyway, I came across the synthesis of acetaminophen, commonly known as paracetamol. It is sold as an over-the-counter drug that is used as a pain reliever and a fever reducer.
The synthesis of this compound involves 3 steps with the starting material as phenol. Below is the mechanism of how the product, paracetamol, is formed.
The very first step in the process is a nitration process. Because the -OH group is an ortho and para director and an activator of the benzene ring, the products formed from the reaction is the ortho- and the para-nitrophenol. The para-nitrophenol is taken to the next step of the reaction process where the nitro group is reduced to form 4-hydroxyaniline. This is possibly achieved by H2 with Pd-C, Fe with HCl or Sn with HCl. The last step of the process involves the addition of -COCH3 group with the help of AC2O to obtain the final desired product, paracetamol.
If you want to know more about the drug and the history behind it, here is the link to it. Enjoy!
http://www.pharmainstitute.in/drug%20of%20the%20month%20july.htm
A.E. =)
I had similar problems with finding an article that did not require a fee. I found your synthesis to be interesting because it is used in over the counter drugs. Always fascinating and fun to learn about how drugs are made. The only question I had was do you know how they go about separating the ortho from the para-nitrophenol so the ortho doesn't move onto the next step. Other than that, good job, and congrats on finding a synthesis.
ReplyDelete-The High School Chemist
Congrats Amra, you found the synthesis of acetaminophen (otherwise known as Tylenol).
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