Hass-Bender-Oxidation

Die Hass-Bender-Oxidation, benannt nach den Chemikern Henry B. Hass und Myron L. Bender, ist eine Namensreaktion aus dem Bereich der organischen Chemie und wurde 1949 erstmals beschrieben.[1] Die Hass-Bender-Oxidation ermöglicht die Darstellung von substituiertem Benzaldehyd aus substituierten Benzylhalogeniden und 2-Nitropropan.

Übersichtsreaktion

Die Hass-Bender-Oxidation verläuft über eine O-Alkylierung des 2-Nitropropan durch (ggf. substituierte) Benzylhalogenide,[2] gefolgt von der Eliminierung eines Ketooxims:[3]

Hass-Bender-Oxidation Übersichtsreaktion V4
Hass-Bender-Oxidation Übersichtsreaktion V4

Reaktionsmechanismus

Der nachfolgende Reaktionsmechanismus wird in der Literatur[4] beschrieben und wird beispielhaft an Benzylchlorid erläutert:

Hass-Bender-Oxidation Mechanismus V2
Hass-Bender-Oxidation Mechanismus V2

Mit Natronlauge wird unter Wasserabspaltung zunächst das Salz des 2-Nitropropans (1) gebildet. Über eine O-Alkylierung mit Benzylchlorid kommt es zur Bildung von Verbindung 2. Durch Eliminierung des Ketoxims (3), entsteht schließlich Benzaldehyd (4).

Einzelnachweise

  1. ↑ H. B. Hass und Myron L. Bender: The Reaction of Benzyl Halides with the Sodium Salt of 2-Nitropropane. A General Synthesis of Substituted Benzaldehydes In: J. Am. Chem. Soc. 71, 1949, S. 1767–1769, doi:10.1021/ja01173a066.
  2. ↑ Malcolm Bersohn: C versus O Alkylation in the Case of a Stable Cation In: J. Am. Chem. Soc. 83, 1961, S. 2136–2138, doi:10.1021/ja01470a022.
  3. ↑ Alfred Hassner und Irishi Namboothiri: Organic Syntheses Based on Name Reactions: A Practical Guide to 750 Transformations, Elsevier, 2012, ISBN 978-0-08-096630-4, S. 203.
  4. ↑ Zerong Wang: Comprehensive Organic Name Reactions and Reagents, Wiley, 2009, ISBN 978-0-471-70450-8, S. 1335–1337.

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