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Synthesis of ring‐ 14 C‐labelled 4(3′‐, 6′‐dimethyl‐3′‐heptyl)‐phenol
Author(s) -
Lalah J. O.,
Lenoir D.,
Henkelmann B.,
Hertkorn N.,
Günther K.,
Schramm K.W.,
Kettrup A.
Publication year - 2001
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.474
Subject(s) - chemistry , anisole , phenol , alkylation , bromide , ring (chemistry) , yield (engineering) , ether , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Ring‐ 14 C‐labelled 4(3′‐, 6′‐, dimethyl‐3′‐,heptyl)‐phenol (NP), an isomer of paranonyl phenol was synthesized for use in aquatic toxicity and metabolism studies. A very efficient method involving alkylation of ring‐ 14 C‐labelled anisole and tertiary alkyl bromide (3‐bromo‐3,6‐dimethyl heptane) with AlCl 3 followed by cleavage of the resultant ether with BBr 3 was used giving a 24% yield ring labelled 14 C‐NP (specific activity: 16.205 MBq/mg and purity >95% by HPLC) after TLC separation. Copyright © 2001 John Wiley & Sons, Ltd.