Never had any luck with the Mg(OMe)2 method...Or chloromethylation for that matter. At least a dozen attempts were tried for each, but with one caveat - The CH2=O donors were less than ideal. Porta-potty grade (in varying states of purity) p-aldehyde and sym-trioxane were used, but neither one gave anything but greenish tar or a polymerized sponge. The work over at SMDB on the Mg(OMe)2 method shows great promise, but I think they neglegcted to realize the necessity of PURE paraformaldehyde in the reaction. All the articles I've dug up go into great detail on the need for anhydrous conditions, the speculative mechanisms backing this up, but none ever touched on the need for pure paraformaldehyde (although this is of no concern in an academic lab anyways)...
...Been looking in a different direction, though - Pure mequinol is not particularly difficult, but working with it leads to some interesting conditions and workups down the line. Been looking more towards p-di-meo-benzene as a starting point. Impure mequinol was used as a precursor in an MeBr methylation ala painkilla - The workup is in progress, but the results look moderately promising - Eyeballing a ~60% yeild despite far less than optimal conditions.
...Once the product is obtained, it will be brominated to 2,5-dimethoxybromobenzene - From there, I see two realistic pathways - The modified duff, and bromomethylation. Been searching up and down for the old bromomethylation thread from the hive, but I can't seem to find it. Anyone have any experience with this, or better yet the thread I'm looking for or a valid link to one of the hive archives?
