Why is a hydroxyl group more activating than a methoxy group in electrophilic aromatic substitution?

Question

Why is phenol more reactive towards electrophilic substitution than methoxybenzene? Isn't the lone pair on the methoxy group oxygen more available for participating in resonance into the ring than the lone pair on hydroxyl oxygen due to the +*I* effect of the methyl group? Or is it because of the steric hindrance of the methoxy group that will favour lesser substitution at the *ortho-* position of the benzene ring? Does the hydrogen bonding of phenol have anything to do with this?

Answer 1

Anisole is actually fairly reactive as well, but why isn't it used as much in industry? While anisole is a little more hydrophobic than phenol, the real reason lies in that industry generally avoids the use of ethers, due to their tendency to form explosive peroxides in storage or form crystalline deposits that are harder to detect in industrial equipment compared to glass.