[carotis]

So, I want to produce 4-Phenylbutanoyl chloride
My master plan needs to start from the hell a lot of benzene I have 
So... I first thought of using butylene lithium reagent to make it attach to the ring.
Now I wonder: wouldn't lithium itself substitute with the ring, due to its difference in elecronegativity? So the result would be a metalation or not? 

[carotis]

Forget about it! It's a benzene, not a cyclohexane, so... the connection can't occur if there is no carbonyl group, isn't that so? I was thinking in the complete wrong direction, about making it aattach and then Clemmesen-Reduction of the Carbonyl group.
The other way around I could think of is using Friedel-Crafts-reaction, then Ozonolysis with H2O2 and finaly COOH I get rid off with SOCl2.
Is it ok so?

[kriggy]

I suppose you could go with FC using succinic anhydride, then reduce the ketone and then run chlorination. (If you can/want run different that using Li reagent)

[beardy]

[carotis]

thanks! I see you yoused Wolff Kishner reduction, nice!

[beardy]

thanks! I see you yoused Wolff Kishner reduction, nice!

 

[Enthalpy]

Would it be conceivable to use an acid chloride longer by one carbon, then abstract the CO using light from lp-Hg, XeBr or XeCl? That would avoid hydrazine. OK, boranes aren't much better anyway.

[kriggy]

What about this guys?

[carotis]

Clemmesen reduction.. that was basically my first approach by synthetizing more complex structures.