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Alkylaluminium Dichloride Induced Friedel-Crafts Acylation of Unsaturated Carboxylic Acids and Alcohols

✍ Scribed by Metzger, Jürgen O. ;Biermann, Ursula

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 575 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1993199301105

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✦ Synopsis

Abstract

The ethylaluminium dichloride induced Friedel‐Crafts acylation of unsaturated carboxylic acids, for example 10‐undecenoic acid (1a) and oleic acid (5a), and of the respective alcohols 1b and 5b with acyl chlorides and cyclic acyl anhydrides gave the corresponding long‐chain β,γ‐unsaturated ketones 3, 6/7, 11 and 13/14 with ω‐carboxy and ω‐hydroxy functions, respectively. The intramolecular cyclization of petroselinic acid chloride (17) yielded (E)‐2‐dodecylidenecyclohexanone (18). Catalytic hydrogenation gave the respective saturated ketones 4, 8/9, 12, 15/16 and 19.

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