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Synthesis of the Sweetener Dulcin from the Analgesic Tylenol

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Brian D. Williams , Birute Williams and Louise Rodino

Department of Chemistry & Physics, King''s College, Wilkes-Barre, PA 18711

J. Chem. Educ., 2000, 77 (3), p 357

DOI: 10.1021/ed077p357

Publication Date (Web): March 1, 2000

Section:

History, Education, and Documentation

Abstract

A sequence suitable for the undergraduate and high school laboratory has been developed for the synthesis of the sweetener dulcin from the analgesic acetaminophen. The analgesic phenacetin is isolated during the synthesis as an intermediate and consequently the experiment can be adopted as a multistep synthesis or as either of two single-period transformations. The sequence described can be performed on either the micro or macro scale and highlights such fundamental organic transformations as amide hydrolysis, Williamson synthesis of phenyl ethers, and a nucleophilic addition of an aryl amine with an isocyanate resulting in carbon-nitrogen bond formation. Numerous essential laboratory techniques are emphasized, including stoichiometric calculations, vacuum filtration, and recrystallization. Analysis of active reaction mixtures and products can be performed using GC, IR, NMR, and TLC.

Keywords (Audience):

High School / Introductory Chemistry

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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