When yau add the Alc. solution to the Na two reaction are running. One, the red. of the acid and two the formation of NaOMe (or NaOEt).
You want the reaction to go fast, else you are just making NaOMe, thats why the OS. synt melt the sodium and let it solidfy into a slurry.
Wather in the alcohol lower the yeald alot, so you dont want anny wather in the alcohol. The point with Na is to make the wather to NaOH and H2 (Na+H2O->NaOH+½H2)
Xylene=xylol will work as well as the solvent.
So i sugest the following routhe
Put 5g Na into 250mL methanol, let it stir a day or two, we now have a mixture of NaOH NaOMe and MeOH, but no wather, (iff you want the pure dry alcohol just destil it off, but it is not nessecery)
Add 22g(1mol) Na to 250mL xylen. heat until the Na melts, then let it cool under stirring.
Disolve 35g(0.2mol) TMB-acid in 200mL dry methanol. Drip the solution to the Na/Xylen slurry in such a rate that it boils gently (5-10min?)
Let it cool down, add wather and seperate. Wash the xylen two times with wather, dry and ewaporate. You now have TMB-Alcohol (Expected yeald ~60%)
(this is all teory I have no personal experience)