[RobertLBio]

I took the time to write this up in chemdraw so it would be easier to see what I am talking about about when when I go to the mechanism for the Achmatowitcz reaction, the formation of the reactive enol does not make sense to me. I have tried to create it from both sides and still cannot get the right to open correctly. Also it seems to be skipping some steps as there shouldn't really be a reason for a methoxy right attached to ring unless we are skipping a lot correct?

[RobertLBio]

So its easier to see I am posting the relative portion of the mechanism in the post:

I just don't see how those methoxy groups fall off during the enol-tautomerization.

[spirochete]

The step where it says H2SO4 over the arrow, there is also water. And the side product is 2 CH3OH.

The H2SO4 step is acetal hydrolysis. Two of them in a row. There needs to be water. It is almost roughly assumed that H2SO4 contains some water. It doesn't

Also I'm not sure why you are saying enol tautomerization. I'm not seeing any tautomerizations, although I didn't write it out in detail so there's a possibility I am missing something.

[rolnor]

But the H2SO4 is not concentrated, there is some water present?

[rolnor]

Its just acetal hydrolysis and formation of a ring-closed hemiacetal, nothing strange?