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

ABSTRACT: 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.

SUBMITTER: Kawasumi R

PROVIDER: S-EPMC5740180 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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One-step Conversion of Levulinic Acid to Succinic Acid Using I<sub>2</sub>/t-BuOK System: The Iodoform Reaction Revisited.

Kawasumi Ryosuke R Narita Shodai S Miyamoto Kazunori K Tominaga Ken-Ichi KI Takita Ryo R Uchiyama Masanobu M

Scientific reports 20171221 1

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 I<sub>2</sub> 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 oxid ...[more]

PMID: 29269768

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