I want to make an ether bond between the benzene ring of phenol and a hydrocarbon chain containing terminal double bond for further biomedical applications. How can I activate this bonding?
I have just few suggestions for your proposed preparation method:
1. Phenol by nature is a weak acid. Any additive (such as a basic medium) that can increase its acidic behavior would be very helpful for the bonding (ether formation) you desire.
2. Alkenes are more likely to undergo addition reaction than condensation, while the synthesis from acidic phenol is very likely to be a condensation route (more like Williamson's).
I suggest you return to use the Williamson's method of ether synthesis; ie, using alkyl halide rather than direct synthesis from terminal alkene as you stated. First subject the alkenes to addition reaction with HI, HBr or the likes and then follow the Williamson's route as shown in the reaction attached.