[curiouscat]

Is there a viable way to get from this starting molecule to Carvacrol? I'm seeing a reference in an internal report but no links to references etc. I want to figure out if someone just was lazy to reference his sources / reactions. Or whether this is implausible.

I searched the standard sources and can find no reference to this conversion. Even structurally it seems alien as to what reaction this could be.



Even if not a direct, single step, that's OK. I just don't spot any viable route.

Any tips? Just brainstorming at the moment.

[sjb]

Ideas - dehydration of the tertiary alcohol plus aromatisation.

[clarkstill]

No hits for this on scifinder. Overall it would be an oxidation - i think you can (on paper, also not on scifinder!) get to the non-phenol by normal E1 type elimination reactions plus a bit of moving stuff around. I guess either the authors have done some undisclosed oxidative reactions on this, or they just guessed/made it up. Is there any context that might help?

[curiouscat]

Ideas - dehydration of the tertiary alcohol plus aromatisation.

Thanks!  Could be. Through some indirect deduction I have a hunch H2SO4 was the reagent involved.

Worth a shot?

Any other suggestions for hot to aromatize this?

[curiouscat]

Is there any context that might help?

Thanks @clarkstill.

The wider context is a process that starts from this precursor and synthesize Carvavrol.