A finding that opened a route to B-blockers was the discovery that B-blocking activ- ity is retained if an oxygen atom is interposed between the aromatic ring and the side chain. To see this difference, compare the structures of labetalol propranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce this side chain. The first of this new class of drugs was propranolol. and OH ОН 1-Napthol (B-Naphthol) Propranolol

A finding that opened a route to B-blockers was the discovery that B-blocking activ- ity is retained if an oxygen atom is interposed between the aromatic ring and the side chain. To see this difference, compare the structures of labetalol propranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce this side chain. The first of this new class of drugs was propranolol. and OH ОН 1-Napthol (B-Naphthol) Propranolol

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 35CTQ

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Show how propanolol can be synthesized from 1-naphthol, epichlorohydrin
, and isopropylamine.

A finding that opened a route to B-blockers was the discovery that B-blocking activ-
ity is retained if an oxygen atom is interposed between the aromatic ring and the side
chain. To see this difference, compare the structures of labetalol
propranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce this
side chain. The first of this new class of drugs was propranolol.
and
OH
ОН
1-Napthol
(B-Naphthol)
Propranolol

Expert Solution

Step 1

When isopropylamine is treated with epichlorohydrin an amino compound with an epoxide ring is formed.
1-napthol is treated with the epoxide. It gives a protonated alcohol.
By the transfer of proton we get the final product.

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