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Isotopically labelled compounds for hazardous waste site cleanup investigations: Part I. Synthesis of [phenyl‐U‐ 14 C] labelled 2,4‐dinitro‐6‐ sec ‐butylphenol (dinoseb) and [phenyl‐U‐ 14 C] labelled 4‐n‐propylphenol
Author(s) -
Goszczynski Stefan,
Crawford Ronald L.
Publication year - 1991
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.2580290107
Subject(s) - chemistry , nitration , medicinal chemistry , distillation , propionate , organic chemistry
Abstract The Fries rearrangement of [phenyl‐U‐ 14 C] propionate forming a mixture of ortho and para hydroxypropiophenones was followed by steam distillation to separate the isomeric products. A Grignard addition to the ortho isomer and elimination of water from the intermediate carbinol, followed by hydrogenation and nitration, yielded [phenyl‐U‐ 14 C] labelled dinoseb. A Wolff‐Kishner reduction of the para isomer furnished [phenyl‐U‐ 14 C] 4‐n‐propylphenol.