[doof]

what is the easiest way to combine two molecules by their methyl group? eg if you wanted to join an alcohol like ethanol or methanol to the methyl group of toluene

[bromidewind]

Are you planning to add the alcohol to the methyl group, or have a methyl group on the alcohol replace the methyl on the toluene? In short, are you trying to form benzyl alcohol (substitution) or phenethyl alcohol (addition)?

I know off the top of my head that oxidation of toluene in an acid with NADPH will give you a good yield of benzyl alcohol (and a few carcinogenic compounds). This is what I remember from biochem as how the body processes toluene. It's probably different in a lab setting, although I would assume the enzyme (I forget which one) used by the body is only a catalyst and is not necessary for the reaction.

Adding ethanol to toluene will give you a double bond in there, since one of the hydrogens has to go. I'm not sure as to what reagents are necessary and how to break that double bond to give you just phenethyl alcohol. Maybe somebody else has a better idea.

[doof]

yeah looking for an addition reaction