[lostengineer]

I am terrible with synthesis. They just do not make sense to me. Here is the problem I am attempting and my attempt at a solution. [Problem and My Attempt][/http://imgur.com/a/2Akz7]. I do not think what I have will work, the benzyne wont react with xylene like I want it to, but I have no idea how to get the solution. I thought about adding the methyl group to xylene first, but don't know how to without adding another carbon. I would really appreciate any help, I have spent hours on this problem and know there is a simple solution. Thanks

Edit: This problem is so frustrating to me, I know there is a simple solution but I do not see it. I'll give a $5 dollar Amazon gift card to anyone who can come up with the solution to help me. I am so lost.

[Arkcon]

Let me help out by attaching the images.  And most of us are glad to help, so you can hang on to the Amazon gift certificate for yourself. 

[lostengineer]

I've completely reworked it, will this synthesis work?
http://imgur.com/Tnt70YL

[orgopete]

This looks like a problem in Diels-Alder chemistry (or electrocyclic reactions). If so, then I would try to draw a suitable diene/dienophile pair. Hint, one has been drawn.

[lostengineer]

That's what I originally thought, but wasn't thinking right. To get the two double bonds on o-xylene could I add Br2 and then use something like KOH to remove the Br to get 5,6-dimethylenecyclohexa-1,3-diene, then react with benzene to get anthracene and then add MeI? Would that be suitable? Did anyone see my second attempt that used mostly Friedel Craft, would that also work? Thanks again for any help

[orgopete]

I think you are on the right track, but I'd add the methyl group earlier as I'm not sure where it inserts in a Friedel-Crafts reaction.

[kriggy]

Wouldnt the FC alkylation in the end yield some crazy mixture of products? I mean, every methyl group activates the system more to the electrophilic substitution.
Is there a way to maybe selectively oxidize the 9 position to alcohol and then do a coupling reaction?

[orgopete]

Re: Friedel-Crafts
I agree. I don't know the preference, but I did not expect preference for 9-alkylation. I didn't look thus up though.

I thought it would be easier to introduce the methyl group early.

[kriggy]

lostengineer: and what topics are you going through right now in your class?
I have 2 possible solutions (at least on paper) but both require one additional organic reagent. Does it work to make grignard reagent from alkyl iodide? Or is it better to use bromide/chloride?
I dont think this the right solution but anyway..

Im not sure if the acetal is stable in basic enviroment so the reduction of the unprotected group might be done differently

[lostengineer]

It is over the entire course, it encompasses everything in the text, I think I am going to use the FC and add the methyl earlier than the last step. Thank you all so much for the help, I really appreciate it.