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1,3‐dihydroxybenzene‐2‐ 13 C: Its preparation and reaction with chlorine and bromine in aqueous solution
Author(s) -
Boyce Scott D.,
Barefoot Aldos C.,
Hornig James F.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200211
Subject(s) - chemistry , aqueous solution , bromine , chlorine , halogenation , sodium methoxide , reagent , organic chemistry , bromoform , chloroform , inorganic chemistry , catalysis , dehydrogenation , methyl iodide , magnesium , medicinal chemistry
1,3‐cyclohexanedione‐2‐ 13 C was prepared by intramolecular Claisen condensation of methyl 5‐oxohexanote‐6‐ 13 C with sodium methoxide. Formation of the ketoester starting material involved treatment of a mixed dicarboxylic anhydride with an isotopicallylabelled Grignard reagent, methyl‐ 13 C magnesium iodide. Dehydrogenation of carbon‐13 labelled cyclohexanedione over a palladium/carbon catalyst produced 1,3‐dihydroxybenzene‐2‐ 13 C. Chlorination and bromination of dihydroxybenzene in aqueous solution yielded isotopically‐labelled chloroform and bromoform, each having enriched carbon‐13 contents equivalent to that of the organic substrate.