Following is a retrosynthetic analysis for propoxyphene, the hydrochloride salt of which is Darvon. The naphthalenesulfonic acid salt of propoxyphene is Darvon-N. The config- uration of the carbon in Darvon bearing the hydroxyl group is S, and the configuration of the other stereocenter is R. Its enantiomer has no analgesic properties, but it is used as a cough suppressant. Me. Me Me. Me Me, Me 3 Ph Ph HO Ph Ph Ph Ph Ph 1-Phenyl-1-propanone (Propiophenone) Propoxyphene

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
Chapter23: Amines
Section: Chapter Questions
Problem 23.57P
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Propose a synthesis for propoxyphene from 1-phenyl-1-propanone and any other necessary reagents.

Following is a retrosynthetic analysis for propoxyphene, the hydrochloride salt of which
is Darvon. The naphthalenesulfonic acid salt of propoxyphene is Darvon-N. The config-
uration of the carbon in Darvon bearing the hydroxyl group is S, and the configuration
of the other stereocenter is R. Its enantiomer has no analgesic properties, but it is used
as a cough suppressant.
Me.
Me
Me.
Me
Me,
Me
3
Ph
Ph
HO
Ph
Ph
Ph
Ph
Ph
1-Phenyl-1-propanone
(Propiophenone)
Propoxyphene
Transcribed Image Text:Following is a retrosynthetic analysis for propoxyphene, the hydrochloride salt of which is Darvon. The naphthalenesulfonic acid salt of propoxyphene is Darvon-N. The config- uration of the carbon in Darvon bearing the hydroxyl group is S, and the configuration of the other stereocenter is R. Its enantiomer has no analgesic properties, but it is used as a cough suppressant. Me. Me Me. Me Me, Me 3 Ph Ph HO Ph Ph Ph Ph Ph 1-Phenyl-1-propanone (Propiophenone) Propoxyphene
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