Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate

Anchimerically Assisted Cleavage of Aryl Methyl Ethers by Aluminum Chloride‐Sodium Iodide in Acetonitrile

“…In our previous work, protocatechuic acid was separated as the major product along with minor 5 h (31%) when treating 4 h with AlI 3 ‐DIC . That reaction was later optimized using ethyl acetate as a sacrificial ester . 2‐Methoxy‐5‐nitrophenol ( 4 j ) was deprotected under the conditions in moderate yield.…”

Cleavage of ethers and demethylation of lignin in acidic concentrated lithium bromide (ACLB) solution

“…Iodic reagents such as iodocyclohexane and trimethylsilyl iodide are also effective for the demethylation [36][37][38][39] . Besides, BBr 3 and AlI 3 can demethylate lignin at room temperature [40][41][42] .…”

Cleavage of Carboxylic Esters by Aluminum and Iodine

“…Methyl benzoate ( 1 ) was selected as the model substrate for the optimization of ester cleaving conditions (Table ). A slight excess of AlI 3 (1.1 equiv), prepared in situ from I 2 and Al, was applied to mediate the demethylation (entries 1–5) following our previous recipes for ether cleavages . Thus, upon treating 1 with iodine (1.65 equiv) and excess Al in MeCN for 18 h at 80 °C, benzoic acid ( 2 ) was obtained in 99% yield (entry 1).…”