13C NMR Analysis of an Aqueous Electrophilic Aromatic Substitution (Synthesis of β‑Resorcylic Acid)

Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe–Schmitt reaction), a...

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Bibliographic Details
Published inJournal of chemical education Vol. 100; no. 8; pp. 2981 - 2985
Main Authors McKee, James A., Rowles, Emalie, Koo, Yumee, McKee, James R.
Format Journal Article
LanguageEnglish
Published Easton American Chemical Society and Division of Chemical Education, Inc 08.08.2023
American Chemical Society
Subjects
Aqueous solutions
Carboxylation
Chemical reactions
Chemical synthesis
Dihydroxybenzoic acid
Hazardous wastes
High pressure
NMR
Nuclear magnetic resonance
Organic chemistry
Phenols
Reagents
Solvents
Substitution reactions
Waste management
NMR Spectroscopy
Hands-On Learning/Manipulatives
Upper-Division Undergraduate
Laboratory Instruction
Second-Year Undergraduate
Green Chemistry
Organic Chemistry
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Summary:Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe–Schmitt reaction), although aqueous, typically involves conditions (high pressure/temperature) that are not well-suited for a large teaching laboratory. The following experiment modifies the Kolbe–Schmitt process for ambient pressures and aqueous reflux temperatures. This procedure is safe, simple, and inexpensive and uses 13C NMR as an analytical tool to confirm product synthesis and investigate changes in molecular symmetry.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.2c00165