Given this retrosynthetic analysis, propose a synthesis for labetalol from salicylic acid and benzyl chloride. [Note: The conversion of salicylic acid to (E) involves a Friedel-Crafts acylation in which the phenolic -OH must be protected by treatment with acetic anhydride to prevent the acylation of the -OH group. The protecting group is later removed by treatment with KOH followed by acidification.] Following is the structural formula of the antihypertensive drug labetalol, a non-specific B-adrenergic blocker with vasodilating activity. Members of this classhave received enormous clinical attention because of their effectiveness in treatinghypertension (high blood pressure), migraine headaches, glaucoma, ischemic heartdisease, and certain cardiac arrhythmias. This retrosynthetic analysis involves dis-connects to the a-haloketone (B) and the amine (C). Each is in turn derived from asimpler, readily available precursor.OHHN.PhPhH,NN.H,NНОНОLabetalol(A)CI+H,N.Ph >PhH,NНО(В)(C)(D) EtO,CH,NPhНО(E)(F)НОНОPhCH,CISalicylic acidBenzyl chloride

The synthesis method of labetalol is shown below,

Answered: Following is the structural formula of…

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Given this retrosynthetic analysis, propose a synthesis for labetalol from salicylic acid and benzyl chloride. [Note: The conversion of salicylic acid to (E) involves a Friedel-Crafts acylation in which the phenolic -OH must be protected by treatment with acetic anhydride to prevent the acylation of the -OH group. The protecting group is later removed by treatment with KOH followed by acidification.]

Following is the structural formula of the antihypertensive drug labetalol, a non-
specific B-adrenergic blocker with vasodilating activity. Members of this class
have received enormous clinical attention because of their effectiveness in treating
hypertension (high blood pressure), migraine headaches, glaucoma, ischemic heart
disease, and certain cardiac arrhythmias. This retrosynthetic analysis involves dis-
connects to the a-haloketone (B) and the amine (C). Each is in turn derived from a
simpler, readily available precursor.
OH
H
N.
Ph
Ph
H,N
N.
H,N
НО
НО
Labetalol
(A)
CI
+
H,N.
Ph >
Ph
H,N
НО
(В)
(C)
(D)

EtO,C
H,N
Ph
НО
(E)
(F)
НО
НО
PhCH,CI
Salicylic acid
Benzyl chloride

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