DISCLAIMER: I am not using any of this information to commit a crime, my university has a license from the relevant authorities to investigate clandestine chemical procedures.
We are investigating an amateur conversion eugenol to the 4-(2-bromopropyl)catechol compound you see there. In theory concentrated hydrogen bromide should be able to cleave the ether, yielding methyl bromide, which can be easily removed from the system, and also add to the double bond in markovnikov fashion. I have some questions for how this reaction can be performed. First of all, what solvent should be used? I am thinking of using acetic acid but i am slightly worried about acetate as a competing nucleophile, especially considering that eugenol acetate (alcohol replaced with acetic ester) is a naturally occurring component of clove oil meaning it must be somewhat stable. Perhaps I would need to take my impure product containing acetate derivatives and treat it again with HBr to fix it a little bit? Also, at what temperature should this reaction be performed? Please help answer me so we can stop the illicit drug trade.