0 votes
26 views
ago in Organic Chemistry by (510 points)
Using retrosynthetic analysis, outline a viable multi-step synthesis of ibuprofen from commercially available starting materials. Include appropriate reagents and conditions.

1 Answer

0 votes
ago by (270 points)
Ibuprofen has the molecular formula C13H18O2 and is a widely used nonsteroidal anti-inflammatory drug  NSAID . A viable multi-step synthesis of ibuprofen from commercially available starting materials can be achieved through the following retrosynthetic analysis:1. Starting material: Iso-butylbenzene  commercially available 2. First step: Friedel-Crafts acylation   Reagents: Acetyl chloride  CH3COCl  and aluminum chloride  AlCl3    Conditions: Anhydrous conditions, room temperature   Product: 4'-isobutylacetophenone3. Second step: Reduction of the carbonyl group   Reagents: Sodium borohydride  NaBH4    Conditions: Methanol  MeOH  as solvent, 0C to room temperature   Product: 4'-isobutyl-1-phenylethanol4. Third step: Conversion to the corresponding carboxylic acid   Reagents: Potassium permanganate  KMnO4    Conditions: Aqueous solution, reflux   Product: 4'-isobutyl--methylbenzylcarboxylic acid5. Fourth step: Conversion to the corresponding acid chloride   Reagents: Thionyl chloride  SOCl2    Conditions: Anhydrous conditions, reflux   Product: 4'-isobutyl--methylbenzylcarbonyl chloride6. Fifth step: Formation of the final product  ibuprofen    Reagents: Sodium salt of 2-methylpropionic acid  prepared by treating 2-methylpropionic acid with sodium hydroxide    Conditions: Anhydrous conditions, room temperature   Product: IbuprofenThis synthesis route involves five steps, starting from commercially available iso-butylbenzene and using well-established reactions and reagents. The overall yield can be optimized by carefully controlling reaction conditions and purifying intermediates as needed.
Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...