title: First synthesis of [1,3,5-(13)C3]gallic acid.
abstract: An efficient and high-yielding synthesis for [1,3,5-(13)C(3)]gallic acid from non-aromatic precursors is presented. [3,5-(13)C(2)]4H-Pyran-4-one was first prepared from the reaction between triethyl orthoformate and [1,3-(13)C(2)]acetone. The third (13)C-atom was introduced into the ring by reaction of the pyranone with diethyl [2-(13)C]malonate. The resulting ethyl 4-hydroxy-[1,3,5-(13)C(3)]benzoate was brominated in the 3- and 5-positions to give ethyl 3,5-dibromo-4-hydroxy-[1,3,5-(13)C(3)]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-(13)C(3)]gallic acid. The synthesis of [2,6-(13)C(2)]4H-pyran-4-one is also presented to demonstrate the potential of the methodology for the regioselective placement of (13)C-atoms into benzene rings.
authors.affiliation: School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, Scotland.
authors.forename: Laura J
authors.initials: LJ
authors.lastname: Marshall
authors.forename: Karl M
authors.initials: KM
authors.lastname: Cable
authors.forename: Nigel P
authors.initials: NP
authors.lastname: Botting
mesh_terms: D001554:Benzene; D002247:Carbon Isotopes; D005707:Gallic Acid / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods*
chemical_list: D002247:Carbon Isotopes; D005707:Gallic Acid; D001554:Benzene