[davidenarb]

Hi all,

consider please the reaction bellow.
polyalkyation occured since alkyl groups are activators and they are para ortho directors (ortho cannot be observed due to steric reasons). If I want to avoid the formation of polyalkylation, is it possible tu use the blocking group technique to have monoalkylation (for example installing so3h and then directing the terbutyl in the meta postion. next, I remove the blocking group with dillute H2SO4) ?

Thank you

[Hunter2]

I think the alcylation still works with sulfonic acids. But to remove -SO₃H with dilutetd sulfuric doesnt work at all.

[davidenarb]

Bellow is the reduction of a product obtained from Friedel Crafts Acylation.
We can see clearly that 2 protons are installed in the benzylic position, so therefore it is impossible to achieve terbutylbenzene with Acylation followed by a reduction

[kriggy]

You could do grignard reaction to get 2nd alkyl chain and then some kind of cross coupling reaction after converting the OH group to halogen or triflate.
You could also use excess of benzene which should be easy to separate from your product