Eugenol to Homogenol (3-EtO-4-OH-Allylbenzene)
(Rated as: excellent)
Synthesis of 3-Ethoxy-4-Hydroxy-Allylbenzene from 3-Methoxy-4-Hydroxy-Allylbenzene (Eugenol)
Bull. Chem. Soc. Japan 11, 179-184 (1936) (../rhodium/pdf /eugenol2homo
I found this article in an abstract database, where they only told that it contained a procedure for converting the Methoxy group of Eugenol to the Ethoxy homolog (called Homogenol by the authors), with no further details given. Great, I thought, then it most definitely contains a procedure for demethylation of eugenol to form 3,4-Dihydroxyallylbenzene (5-allylpyrocatechol), an excellent precursor to safrole. However, when I actually found the article, I saw that it contained a rather byzantine route for the insertion of that extra CH2 group.
However, the article contains some rather interesting chemistry anyway, and various compounds which very likely can be used as precursors to other substances than safrole.