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I have to synthesis the above compound using only toluene as the carbon source. 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 2 phenyl groups are meta substituted despite having a methyl group which is suppose to be ortho and para directing.

Could someone please give me some tips and hints on how to start this question. Or at least give me the name of the molecule so that I can see what I can find about it on the web.

Edit 1

From the answer below it states I need to use Fridel-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:

enter image description here

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

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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.

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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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  • $\begingroup$ thanks for you answer. For the acylation step, do you mean that I need to convert toluene into benzoic acid using KMnO4 and then react half of it with SOCl2 to form C6H5COCl. Then react that with the other half of the benzoic acid? $\endgroup$ – Nanoputian Feb 21 '16 at 5:35

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