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Functional polymers, XL. Syntheses of mono- and di(4-methoxy)benzotriazolesubstituted 2,4-dihydroxyaceto(or benzo)phenones

Funktionelle Polymere, 40. Mitt.: Synthese von mono- und di(4-methoxy)benzotriazol-substituierten 2,4-Dihydroxyaceto(oder benzo)phenonen

  • Organische Chemie Und Biochemie
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Abstract

Eight benzotriazoles and (4-methoxy)benzotriazoles, mono- or di-substituted derivatives of 2,4-dihydroxyaceto(or benzo)phenone were synthesized by azo coupling of (4-methoxy)2-nitrobenzenediazonium chloride with 2,4-dihydroxyaceto(or benzo)phenone followed by reductive cyclization. Pure mono-substituted compounds were very difficult to prepare. Careful selection of thepH for the azo coupling and selection of the proper reagents for the reductive cyclization were essential. All compounds were characterized by their ultraviolet, infrared1H and13C NMR spectra and their elemental analysis. These compounds have both the 2(2-hydroxyphenyl)2H-benzotriazole unit and a 2-hydroxyaceto(or benzo)phenone unit in the same molecule and are effective and useful ultraviolet absorbers.

Zusammenfassung

Es wurden acht Benzotriazole und 4-Methoxybenzotriazole — mono- oder disubstituierte Derivate von 2,4-Dihydroxyaceto(oder benzo)phenonen — über Azokopplung von 4-Methoxy-2-nitrobenzoldiazoniumchlorid mit 2,4-Dihydroxyaceto(oder benzo)phenonen und nachfolgender reduktiver Cyclisierung synthetisiert. Reine monosubstituierte Verbindungen waren sehr schwer herzustellen. Sorgfältige Wahl despH-Wertes für die Azo-Kupplung und geeignete Reagentien für die reduktive Cyclisierung waren dabei wesentlich. Alle Verbindungen wurden mittels UV-, IR-,1H-NMR- und13C-NMR-Spektren und Elementaranalysen charakterisiert. Die synthetisierten Verbindungen besitzen jeweils eine 2-(2-Hydroxyphenyl)-2H-benzotriazol-Einheitund eine 2-Hydroxyaceto(oder benzo)phenon-Einheit im gleichen Molekül und stellen effektvolle und nützliche Ultraviolett-Absorber dar.

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Authors and Affiliations

  1. Polytechnic Institute of New York, 11201, Brooklyn, NY, USA

    Shoukuan Fu, Shanjun Li & Otto Vogl

Authors
  1. Shoukuan Fu
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  2. Shanjun Li
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  3. Otto Vogl
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Dedicated to Prof. Dr.K. Komarek, Vienna, on the occasion of his 60th birthday with best wishes.

Part XXXIX:S. K. Fu, A. C. Albertsson, A. Gupta, andO. Vogl, in: New Trends in Photochemistry of Polymers (N. S. Allen andJ. F. Rabek, eds.), 1985, p. 247.

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Fu, S., Li, S. & Vogl, O. Functional polymers, XL. Syntheses of mono- and di(4-methoxy)benzotriazolesubstituted 2,4-dihydroxyaceto(or benzo)phenones. Monatsh Chem 117, 805–819 (1986). https://doi.org/10.1007/BF00810072

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  • DOI: https://doi.org/10.1007/BF00810072

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