Recently, I am struggling with following reaction (attempt). I have a molecule which contains both, a methyl phenyl ether group and an aliphatic ether chain. For subsequent reactions, I would like to cleave the aryl methyl ether group to obtain a phenol.
So far I tried cleavage with a) high excess AlCl3 in DCM anh. at RT, and b) 1.1 eq AlCl3 with 3 eq NaI in MeCN anh. at RT. However, neither pathway worked. Since the aliphatic ether oxygen atoms are more basic, I suspect them to form Lewis acid-base complexes R2O->AlCl2 first. That is also, why I haven't tried the classic BBr3 so far, in fear of it cleaving the aliphatic ether already at RT.
Do you have experience/suggestions with selective ether cleavage reactions? Greetings.