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The synthesis of carbon‐14 labeled 1‐(4,8‐dimethyl‐8‐methoxynonyl)‐4‐(1‐methylethyl)benzene
Author(s) -
Aguinaga Guillermo M.,
Dinizo Stephen E.
Publication year - 1987
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.2580240513
Subject(s) - chemistry , wittig reaction , benzene , benzaldehyde , ring (chemistry) , isopropyl , catalysis , catalytic hydrogenation , organic chemistry , medicinal chemistry , carbon fibers , materials science , composite number , composite material
The title compound, uniformly labeled with carbon‐14 in the benzene ring, was prepared by Wittig reaction of 4‐isopropyl‐benzaldehyde‐ 14 C ring (U) with 3,7‐dimethyl‐7‐methoxyoctylidene‐tripehylphosphrane followed by catalytic hydrogenation of the resulting mixture of olefins. A second route to the title compound, based on alkyllithium chemistry, was demonstrated using unlabeled intermediates. Attempted preparation of the title compound via the Horner‐Emmons modification of the Wittig reaction was unsuccessful.