Abstract
Using eugenol and vanillin as model substrates, a practical method is developed for
the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from
aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species.
The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl
ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of
functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen
are well tolerated under the optimum conditions. Partial hydrodebromination was observed
during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as
an acid scavenger. This convenient and efficient procedure would be a practical tool
for the preparation of catechols.
Key words
acid scavenger - aluminum oxide iodide - demethylation - eugenol - hydrodebromination
