Alright you organic chem guru's I've got a question for you. Now I've thought about this a bit and did some research but keep getting stuck in 'chem loops'.

Now whether or not methyl tosylate works for phenolic substrates isn't  debate-able. Base catalyzed phenoxide formation, and a typical SN2 ensues(hopefully I didn't get to cocky but I'm pretty sure this is how this works). This is certainly most useful for methyl and benzyl aryl ethers, so there is no competing elimination reaction(as I understand it at least ).

The tricky part is the aldehyde moeity and the base/solvent used. To show that I am not asking for spoon-feeding here are some of my thoughts(none of which are fruitful so feel free to skip down to the best idea part).

For example, acetone cannot be a solvent due to base catalyzed  condensation reactions are higher temperatures, throwing an aldehyde in there sounds like its begging for undesired condensation products as well as enolates? Also K2CO3 dries acetone so that's not really a safe bet and likely boils to low for this reaction to procede reasonably? Aldehydes forms a reversable schiff bases with 1* and 2* amines such so perhaps a tertiary amine? Suppose a schiff-base could be hydrolyzed back with a weak acid to prevent acetal formation. However, a solvated ionic base would probably aid phenoxide formation greater then a tertiary amine(haven't checked pKas in solvents or anything). (chem 'loops' start happening about here)

Best idea eye have:
Maybe form the acetal as a protecting group the procede with the alkylation that will not be reversible in basic conditions? Then remove the acetal in acid after?

Essentially I'm wondering if anyone can find any references for this being done, or is my best idea the most 'solid'?

So forming the acetal is not necessary?

I do have access to methyl tosylate. A substrate test is always a good idea, I'll have to find one to play with before putting my reagent where my mouth is.

I have a bit of DMSO hanging around but it's oxidized and sounds a serious stinky pain to dry. DMF would be nice to have for a few reasons but NMP, or MEK might be more practical in finding OTC and drying. Thanks for the tip on the acetone.

I didn't realize an inert atmosphere would be necessary, that will likely delay things.

Excellent. Will get on this as soon as possible and report back . Will check via TLC and melting points. Yea NMP sounds best for now. Doubt that lactam will open from K2CO3, however it does have a rather high boiling point which could make work-up painful. Who knows, the reaction may even procede reasonably at STP. For N-Alkylation I've seen alkyl tosylates used at 'high-temperatures' for long periods of time iirc. Totally different substrate though, we'll see.

To be honest I find the lack of information involving alkyl tosylates and aryl ether formation a bit curious. I'm not new to the persistent trying and 'failing'. Failure to receive product is a success in gaining a better approach to said product. Thanks for the insight as always pyramid.

Toady might suggest vanillin as a substrate aldehyde. Its cheap as dirt, and the methylated product will be useful. Not to mention that its methylated derivative is known in the literature.

And non-toxic to boot. Although when methylating agents/alkylating agents in general are put in play, the toxicity of the aldehyde goes right out of the window as a consideration, they are all nasty. Some less noxious than others, such as say, trimethyl phosphate, but aside from their insidious carcinogenic toxicity the acute toxicity of some of them, such as Me2SO4 is extreme.

Phenates are air-sensitive? is it specific to this substrate, or does that apply to phenate salts in general? If so..never knew that. What are the typical end products of such an oxidation? if it is an oxidation of course, and not reacting with airborne CO2.