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Regioselective Synthesis of a Branched Isomer of Nonylphenol, 4‐(3′,6′‐Dimethyl‐3′‐heptyl)phenol, and Determination of its Important Environmental Properties
Author(s) -
Lalah Joseph O.,
Schramm KarlW.,
Lenoir Dieter,
Henkelmann Bernhard,
Hertkorn Norbert,
Matuschek Georg,
Kettrup Antonius,
Günther Klaus
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20011119)7:22<4790::aid-chem4790>3.0.co;2-l
Subject(s) - phenol , anisole , chemistry , yield (engineering) , organic chemistry , regioselectivity , vapor pressure , solubility , nonylphenol , friedel–crafts reaction , proton nmr , environmental chemistry , materials science , metallurgy , catalysis
Abstract A method for the synthesis of a pure nonylphenol isomer, 4‐(3′,6′‐dimethyl‐3′‐heptyl)phenol, by Friedel–Crafts reaction between anisole and 3‐bromo‐3,6‐dimethylheptane that gives a 47.3 % overall yield is reported. The reactions were followed by GC‐MS, and the chemical structures are in agreement with the NMR and IR spectra. The log K ow value for this compound, its water solubility, vapor pressure, and Henry's Law constant were also determined. These physicochemical properties were required for prediction of the compound's behavior in aquatic ecosystems.