0 votes
34 views
in Chemical synthesis by (138k points)
What conditions and catalysts are necessary for the successful synthesis of ibuprofen from 2-methylpropylbenzene and carbon dioxide, and what are the intermediate compounds produced during the process?

1 Answer

0 votes
by (138k points)
The synthesis of ibuprofen from 2-methylpropylbenzene and carbon dioxide involves several steps, with different conditions and catalysts required for each step. Here's an overview of the process:1. Friedel-Crafts Alkylation: The first step is the alkylation of the benzene ring in 2-methylpropylbenzene  also known as isobutylbenzene  using propionyl chloride. This reaction requires a Lewis acid catalyst, typically aluminum chloride  AlCl3  or iron III  chloride  FeCl3 . The reaction is carried out at a temperature of around 80C. The intermediate compound produced in this step is 2- 4-isobutylphenyl propanoyl chloride.2. Hydrolysis: The next step is the hydrolysis of the acyl chloride group in the intermediate compound to form a carboxylic acid. This can be achieved by adding water to the reaction mixture and heating it to around 100C. The intermediate compound produced in this step is 2- 4-isobutylphenyl propionic acid, which is also known as -methyl-4- 2-methylpropyl benzeneacetic acid.3. Carboxylation: In this step, carbon dioxide  CO2  is introduced to the reaction mixture to form a new carboxylic acid group. The reaction is carried out under high pressure  around 30 atm  and high temperature  around 150C . A transition metal catalyst, such as palladium  Pd  or nickel  Ni  on a support like activated carbon or alumina, is used to facilitate the carboxylation. The intermediate compound produced in this step is 2- 4-isobutylphenyl butyric acid.4. Decarboxylation: The final step is the decarboxylation of the 2- 4-isobutylphenyl butyric acid to form ibuprofen. This reaction requires heating the reaction mixture to around 230C in the presence of a strong base, such as sodium hydroxide  NaOH  or potassium hydroxide  KOH . The decarboxylation results in the loss of a carbon dioxide molecule and the formation of the final product, ibuprofen.In summary, the successful synthesis of ibuprofen from 2-methylpropylbenzene and carbon dioxide requires a series of reactions with different conditions and catalysts, including Lewis acids  AlCl3 or FeCl3 , transition metal catalysts  Pd or Ni , and strong bases  NaOH or KOH . The intermediate compounds produced during the process are 2- 4-isobutylphenyl propanoyl chloride, 2- 4-isobutylphenyl propionic acid, and 2- 4-isobutylphenyl butyric acid.

Related questions

Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...