Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.

Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.48P

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Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.
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Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-thecounter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.
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