One-step Conversion of Levulinic Acid to Succinic Acid Using I2/t-BuOK System: The Iodoform Reaction Revisited

The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I2 and t-BuOK in t-BuOH, in which in situ-...

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Published inScientific reports Vol. 7; no. 1; pp. 1 - 17967
Main Authors Kawasumi, Ryosuke, Narita, Shodai, Miyamoto, Kazunori, Tominaga, Ken-ichi, Takita, Ryo, Uchiyama, Masanobu
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group 21.12.2017
Nature Publishing Group UK
Subjects
Acids
Carboxylic acids
Demethylation
Ethanol
Succinic acid
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Summary:The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I2 and t-BuOK in t-BuOH, in which in situ-generated t-BuOI serves as the chemoselective iodinating agent. This system enables one-step conversion of levulinic acid to succinic acid, a major four-carbon chemical feedstock. This oxidative demethylation is also applicable to other compounds containing an acetyl group/ethanol unit, affording the corresponding carboxylic acids in a selective manner.
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ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-017-17116-4