I have had the idea once to synthesize sesamol from benzedioxol via diazotation. In my opinion, the B-V reaction of piperonal
sounded to wasteful
I never went any further then the nitration of benzedioxol, which really was no problem. Stupid as I am, I didn't write down the reaction details, but I remember the solvent being GAA and the yield was to be found in the 90s%. GC/MS analysis indicated the presence of ca 1% of a (tentatively identified) dinitrated product, but aside this impurity, everything looked OK. Colour test with concentrated sulfuric acid also matched the literature references in Beilstein (was it red? Not of importance now...).
The idea behind this was to find a precursor for 5-alkoxy-piperonal. Sesamol can be methylated, ethylated... and subsequently thrown in a Vilsmeier-Haack reaction mixture to magically yield 5-alkoxypiperonal.
Bromination of the benzedioxol worked out well, but substitution of the Br by OH (Cu catalyzed) seemed to be a problem... Maybe I should try to find my nitrated benzodioxol in the fridge and look for what it does with the one-pot thing...