Alright. I'd like to start a discussion about going from eugenol directly to safrole. In the past, all routs to safrole from eugenol have involved demethylating the methoxy group, then methylating the two phenols. Why?, I asked. Eugenol already has everything safrole has, the only difference is, the 4 position phenol isn't connected to the 3 postion methoxy. So why go through several steps to get to safrole, when you could just hitch up the methoxy and the phenol in one step?
In the methylation step from catechol-->benzodioxole, a base is used to deprotonate the phenols in order to react the with the methylene halide.
Now, can't the phenol AND the methyl part of the methoxy group be deprotonated at the same time, and with perhaps a sodium halide, or even an elemental halide to react and close the bridge? I've been reading that in order to deprotonate a methyl group if you use a base with a higher pKa than the C-H bond. Now, what I don't know is, what is the pKa of the C-H bods in the 3 position methoxy group of eugenol.(or vanillin) Comments? What bases could be used to deprotonate both the methyl group and the phenol simultaneously? Comments?
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