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

被引：2

作者：

McKee, James A. A. ^{[1
]}

Rowles, Emalie ^{[1
]}

Koo, Yumee ^{[1
]}

McKee, James R. R. ^{[1
]}

机构：

[1] Univ Sci, Dept Chem & Biochem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF CHEMICAL EDUCATION | 2023年 / 100卷 / 08期

关键词：

Second-Year Undergraduate; Upper-Division Undergraduate; Organic Chemistry; Laboratory Instruction; NMR Spectroscopy; Green Chemistry; Hands-On Learning; Manipulatives; KOLBE-SCHMITT SYNTHESIS; CHEMISTRY; GREEN; CARBOXYLATION; SPECTROSCOPY; OXIDATION;

D O I：

10.1021/acs.jchemed.2c00165

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electrophilic aromatic substitution reactions are commonin theorganic chemistry laboratory. These reactions, while ubiquitous, usecorrosive reagents and halogenated or hydrophobic solvents that produceexpensive and hazardous waste streams. The carboxylation of phenols(Kolbe-Schmitt reaction), although aqueous, typically involvesconditions (high pressure/temperature) that are not well-suited fora large teaching laboratory. The following experiment modifies theKolbe-Schmitt process for ambient pressures and aqueous refluxtemperatures. This procedure is safe, simple, and inexpensive anduses C-13 NMR as an analytical tool to confirm product synthesisand investigate changes in molecular symmetry.

引用

页码：2981 / 2985

页数：5

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