Woahhh you got me on the spelling.
Sesamol is 1,3-benzodioxole-5-ol, just so you know for the future.
sooooooo, just run a tosyl substitution for the hydroxy group, and then do an Sn2 under usual conditions. Can also do thionyl chlorination instead but Tsl gets better yields, can also just do a straight up halogenation. Yield for the former is usually around 80% while the latter is mid 60's. This coming from a completely legal chemical by the way.
Anything else you would like to try and correct me on?
Well id say it was more than a spelling error. So a tosyl substitution huh? Good choice for stinking up your apartment and inviting in hazmat crews with your choice of a molar excess of pyridine or triethylamine for the scavenger base. Either one of those chemicals in the amounts needed are gona reek to high heavens not to mention have no commercial use other than organic chemistry. Also a SN2 on an aromatic like that will not yield the fancy leaving group you are interested in but a chloride group. It simply will not make the product you are interested in, in any halfway decent yield. I have references if you are interested.
Either way you are doing two SN2 reactions in a row hoping for halfway decent yields after your intense cleanup and extraction in the last step. These reactions are very solvent, concentration and reactant dependent, something you would know if you ever tried to develop your own reaction scheme. But no its so much easier to just pop open an ochem textbook and point at generic reactions and then try and apply them to your situation, real life isnt that simple.
You literally just pointed to some simple, first year ochem reactions that in the simplest way applied to this situation.
When I was active the one type of person I made sure never to work with was the type that had something to prove. They were worse than the junkies or the loudmouths. They would always end up self-sabotaging because they constantly needed to impress someone or one-up somebody.