Guys,
I've looked for about methylation with methyl iodide to make trimethoxybenzaldehyde. I found somethings, but not exactly what I want.
What I found that's here:
* Quinacetophenona is converted into a monomethyl ether by cooling a solution in acetone to room temperature, adding potassium carbonate and methyl iodide, and refluxing for 6 hrs.
* Carbohydrates are methylated by combination of methyl iodide-silver oxide (barium oxide can replace Ag2O(1)).
Kuhn(2) found that carbohydrates can be completely methylated in a single step by silver oxide and methyl iodide if dimethylformamide is used as solvent. The carbohydrate is dissolved in 10-25 times its weight of DMF and treated at room temperature with MeI (3equiv. per OH group) and silver oxide (2 equiv. per OH group).
Have anybody ever maked trimethoxybenzalheyde form 5-hidroxy-vanillin using methyl iodide? And what were the conditions and the solvent used?
I would appreciate if you give me some information.
Regards,
Bibliography:
Reagents for Organic Synthesis
Louis F. Fieser and Mary Fieser., 682,683 - (1967)
References:
(1) - R. Kuhn, H. Baer, and A. Seeliger. Ann, 611, 236 (1958)
(2) - R. Kuhn, H. Trischmann, and I. Löw, Angew. Chem., 67,32 (1955)