I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions.
See image for the problem.
My first thought was the Dienone-phenol-rearrangement. But in order to do so, I need to add the alkyl substituent and I need a dienone. So can I deprotonate the phenol using potassium carbonate? (Or is it too weak as a base? The pKa of bicarbonate is around 10, so maybe it is too weak) But if it is possible, then the free electron pair of the oxygen can form a ketone... I could then use the alkene with a chloride substituent, so that the aromatic ring can attack it. Then I would have the dienone. But with the Dienone-phenol-rearrangement, the alkyl substituent can only move by one carbon-atom in the ring...
Is my thought process wrong? Can you please help me?
I did not have any lectures on rearrangement reactions, I had to learn them by myself, but by now, I have not found any similar reactions.