Synthesising Complex Aromatic Compound


> 
> Synthesize the following compound using only toluene as the carbon source-
>  [![bis(3-methylphenyl)(phenyl)methanol](https://i.stack.imgur.com/Pq3ZC.png)](https://i.stack.imgur.com/Pq3ZC.png)
> 
> 
> 


I have never done something like this before and I have no clue on how to start. 
I am even more confused by the fact that the top two phenyl groups are meta substituted despite having a methyl group which is suppose to be ortho and para directing. 




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From an answer below it states I need to use Friedel–Crafts acylation. However I am not entirely sure how to do this. This is my guess:


Convert toluene into benzoic acid using $\ce{KMnO4}$ and then react half of it with $\ce{SOCl2}$ to form $\ce{C6H5COCl}$. Then react that with the other half of the benzoic acid followed by Wolff–Kishner reduction to form the below molecule:


[![3-benzylbenzoic acid](https://i.stack.imgur.com/anPGz.png)](https://i.stack.imgur.com/anPGz.png)


After this, I am not sure how to chlorinate it so that I do another acylation. 




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.


[![enter image description here](https://i.stack.imgur.com/FUYwI.png)](https://i.stack.imgur.com/FUYwI.png)


 12

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.


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