Chemistry - Synthesising Complex Aromatic Compound

Solution 1:

An alternative approach might be something like this. The tertiary alcohol product with two identical groups suggests that a Grignard reaction with an ester might be a useful step.

Solution 2:

You'll obviously need meta-directors, so convert those methyl groups into a different function.

I'd start with a benzylic oxidation to get benzoic acid, and work some Friedels-Craft acylation magic.

Then you can reduce the resulting ketone and chlorinate, and go at an acylation again.

Finally a DIBAL and then Wolf-Kichner Reduction to get rid of your carbonyls.

Probably you need to flesh this out some.