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Crystallographic identification of an unexpected by‐product in an Ullman's reaction toward biphenyls: 1‐(4‐hexyloxy‐3‐hydroxyphenyl)ethanone
Author(s) -
Manzano Veronica E.,
Baggio Ricardo,
Cukiernik Fabio D.
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615019919
Subject(s) - chemistry , supramolecular chemistry , biphenyl , molecule , product (mathematics) , crystallography , nuclear magnetic resonance spectroscopy , nmr spectra database , stereochemistry , spectral line , organic chemistry , physics , geometry , mathematics , astronomy
The synthesis of 3,3′‐diacetoxy‐4,4′‐bis(hexyloxy)biphenyl following the nickel‐modified Ullmann reaction yielded a by‐product which was identified successfully by crystallographic analysis as 1‐(4‐hexyloxy‐3‐hydroxyphenyl)ethanone, C 14 H 20 O 3 . This unexpected nonbiphenyl by‐product exhibited IR, 1 H NMR, 13 C NMR and COSY (correlation spectroscopy) spectra fully consistent with the proposed structure. The compound crystallized in the orthorombic Pbca space group, with two independent formula units in the asymmetric unit (one of which was slightly disordered), and showed a supramolecular architecture in which molecules linked by hydroxy–ethanone O—H...O interactions are organized in columns separated by the aliphatic tails.