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Specific 14 c ‐labeled surfactants . The addition of hohogeneous polyoxyethylene glycols to p‐(l,l,3,3‐tetramethylbutyl)phenol
Author(s) -
Tanaka F. S.,
Wien R. G.
Publication year - 1976
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.2580120112
Subject(s) - chemistry , phenol , ethylene oxide , ethylene glycol , medicinal chemistry , chloroacetic acid , moiety , coupling reaction , ether , methylene , organic chemistry , nuclear chemistry , catalysis , polymer , copolymer
Two surfactants, one containing a six and the other containing a nine unit polyoxyethylene glycol side chain attached to p‐(1,1,3,3‐tetramethylbutyl) phenol (TOPOH), were prepared with specific 14 C‐labeling. The radioactive label was introduced into the first ethylene oxide unit attached to the aryl moiety, TOPOCH 2 *CH 2 (OCH 2 CH 2 ) n OH, by coupling chloroacetic‐ 14 C‐l acid with TOPOH. A 4‐step reaction scheme was utilized in the synthesis, and all reactions gave excellent yields except for the final Williamson coupling reaction. A competing elimination reaction occurred in the final reaction to afford a vinylic by‐product, TOPOCHCHCl, which was identified by spectroscopic methods. The overall yields for TOP(OCH 2 CH 2 ) 6 OH and TOP(OCH 2 CH 2 ) 9 OH were 42 and 33 per cent, respectively.