Correct me if Im wrong but I dont think methyl iodide is a a good ally in methylations.
How do you get that impression ?
Methylation of syringaldehyde with MeI :Phytochemistry; 25; 9; 1986; 2093-2102
I am also convinced that it is too weak for the methylation of deactivated oxygens on the phenyl ring (can syringaldehyde be methylated w/meI ?) therefore you have to run the rxn longer and if you are not working under inert atmosphere longer times in alkalis with an access to O2 means oxidation of the phenol therefore yield will drop.
Don't be convinced before you've tried and found out.
No need to mention the evil REAL CARCINOGEN DMS (Dna Methylating Snag )
It is up to you to take the appropriate precautions when preparing or handling DMS or any other toxic/carcinogen/whatever substance. There's fume hoods, goggles, gloves and gas masks - use them together with knowing what you do and how to respond to a leakage or whatever.
Stop whining, take measures.
I dont want to use trimethyl phosphate cuz it never seemed appealing to me (due to the vaccum pyrollysis stage of preperation
What's so damn hard about that preparation ? You mix two compounds, stir, heat, apply vacuum, and distill your product. Standard things to do in an org. chem. lab. The yield could be higher, but given the cheapness of P2O5 and the ease of preparation I rate it among my favorite methylating agents.
its methlyating capacitiy is not worth the hassle
Patent US4453004
Example 1
In a three-neck flask (capacity 100 mL) equipped with a mechanical stirrer and reflux condenser...
Example 4
In an apparatus similar to Example 1, 15.2 g (0.083 mol) of syringaldehyde and 15.0 g (0.11 mol) of potassium carbonate were heated to 105°C under nitrogen and 15 mL (0.12 mol) of trimethyl phosphate were added over 10 minutes. The mixture was maintained at about 80°C for 3 hours then cooled to 45°C and quenched with 50 mL of H2O. The tan solid which precipitated was collected, washed with 3 x 50 mL of water and dried to give 15 g (92%) of 3,4,5-trimethoxybenzaldehyde.
My books mention diazomethane as the most "cute" methylating agent which has only N2 as the byproduct and its as powerful as DMS. But get ready - This is a new door for another disease: CHEMICALLY CAUSED ASHTMA when breathed And it may decide to explode whenever it wants if the storage conditions (esp. the storage bottle which has to be smooth surfaced - projecting glass + diazomethane + movement = EXPLOSION)
You label it cute and give all the reasons why it isn't. It is however a really interesting methylating agent. I never looked into it much.
Concerning the asthma: 1)don't breath it, it's that simple - but yeah, you'll have to invest in a bit of equipment. 2) Is it acute or chronic ?
What more? DMC is impossible to make. It needs explosive setups CO gas or psoghene
I wouldn't say it's impossible to make, just needs some research. It might not be worth the hassle, but that can only be told, if the research (loads of visits to the library) is done.
ARE WE GETTING ARMED FOR WORLD WAR 3?
We better should. Spiritually 
Yeah the alkyl tosylates. Many say its harmless and easy to prepare + work with.
My personal favorites. Synthesis is straight forward. Methylation results are comparable to DMS.
But it wont suprise me if chemists start dying one by one from a newly evoked TOSYLOALOSIS disease.
The general opinion of alkyl tosylates being safer than DMS must have some reason. If you don't want to believe that, treat it like DMS to make free from any doubt.
--psyloxy-
