Jump to main content
Jump to site search

Issue 4, 2009
Previous Article Next Article

First synthesis of [1,3,5-13C3]gallic acid

Author affiliations

Abstract

An efficient and high-yielding synthesis for [1,3,5-13C3]gallic acid from non-aromatic precursors is presented. [3,5-13C2]4H-Pyran-4-one was first prepared from the reaction between triethyl orthoformate and [1,3-13C2]acetone. The third 13C-atom was introduced into the ring by reaction of the pyranone with diethyl [2-13C]malonate. The resulting ethyl 4-hydroxy-[1,3,5-13C3]benzoate was brominated in the 3- and 5-positions to give ethyl 3,5-dibromo-4-hydroxy-[1,3,5-13C3]benzoate. Subsequent hydrolysis of the ester and substitution of the bromine atoms with hydroxyl groups was achieved under basic conditions in a single step to yield the desired [1,3,5-13C3]gallic acid. The synthesis of [2,6-13C2]4H-pyran-4-one is also presented to demonstrate the potential of the methodology for the regioselective placement of 13C-atoms into benzene rings.

Graphical abstract: First synthesis of [1,3,5-13C3]gallic acid

Back to tab navigation

Article information


Submitted
12 Aug 2008
Accepted
25 Nov 2008
First published
12 Jan 2009

Org. Biomol. Chem., 2009,7, 785-788
Article type
Paper

First synthesis of [1,3,5-13C3]gallic acid

L. J. Marshall, K. M. Cable and N. P. Botting, Org. Biomol. Chem., 2009, 7, 785
DOI: 10.1039/B813991A

Social activity

Search articles by author

Spotlight

Advertisements