15674-95-0Relevant articles and documents
Alkylaluminium Dichloride Induced Friedel-Crafts Acylation of Unsaturated Carboxylic Acids and Alcohols
Metzger, Juergen O.,Biermann, Ursula
, p. 645 - 650 (2007/10/02)
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.Key Words: Friedel-Crafts acylation / β,γ-Unsaturated keto carboxylic acids and alcohols