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Preparation of uniformly 14 C‐labeled and 13 C‐enriched catechol and hydroquinone via phenol
Author(s) -
Chew Edward H.,
Heys J. Richard
Publication year - 1981
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.2580180410
Subject(s) - hydroquinone , chemistry , catechol , phenol , benzene , hydrolysis , nitration , organic chemistry , nitrophenol , medicinal chemistry , nuclear chemistry , catalysis
Catechol‐U‐ 14 C and hydroquinone‐U‐ 14 C were prepared from phenol‐U‐ 14 C by mononitration followed by chromatographic separation of o ‐ and p ‐nitrophenol‐U‐ 14 C. The nitrophenols were separately hydrogenated, and the resulting aminophenols were converted by diazotization followed by hydrolysis to the title diols. Phenol‐U‐ 14 C was synthesized efficiently from benzene by nitration, reduction, diazotization and hydrolysis. A similar series of reactions beginning with benzene‐U‐ 13 C gave phenol, catechol and hydroquinone containing more than 88% total carbon‐13.