LEWIS ACID-CATALYZED ADDITIONS TO UNSATURATED FATTY COMPOUNDS .2. ALKYLALUMINUM HALIDE CATALYZED ENE REACTIONS OF UNSATURATED FATTY COMPOUNDS AND FORMALDEHYDE

We are presenting our results on the alkylaluminium halide catalyzed ene addition of formaldehyde to readily available unsaturated fatty compounds to give primary homoallylic alcohols. The reaction of oleic acid and 10-undecenoic acid with formaldehyde gives (E)-9(10)-(hydroxymethyl)octadec-10(8)-enoic acid and 12-hydroxydodec-9-enoic acid, respectively, in high yields. Formaldehyde can be added also to oleyl alcohol to give the very interesting diol (E)-9(10)-(hydroxymethyl)oxtadec-10(8)-en-l-ol. Me2AlCl and EtAl-sesquichloride are the most suitable catalysts for these reactions. The addition of formaldehyde to methyl oleate and methyl 10-undecenoate, respectively, to give the corresponding ene products is catalyzed by EtAlCl2.