Resorcinol and sodium hydride

[Caffeinated Chemist]

I am synthesizing a phenyl ether from an alkyl resorcinol and primary alcohol, however my mentor has suggested a 2-step method that I don't fully understand. I was hoping someone could help me understand the purpose of all the reactants so that I can establish a mechanism before actually trying the reaction.

 

I understand the first step of the reaction. It involves activating a primary alcohol by reacting it with sulfonyl chloride. I already have the mechanism, method, and isolation confidently written out.

 

For the second step, my mentor has suggested taking the alkyl resorcinol and treating it with sodium hydride in a polar aprotic solvent before adding the tosylated alcohol from the first step.

 

Embarrassingly, I cannot say for sure what treating the resorcinol with sodium hydride is supposed to accomplish before addition of the tosylated enolate (Ph-O-+Na?). Can someone please explain to me what this would do? Something that would be even more helpful is if you have a copy of, or link to, a paper in which a similar reaction is carried out.

 

I really appreciate your time! Thank you for any help you can give.

[Knumbnuts]

Well you are correct. You generate the phenoxide anion which is more nucleophillic than the phenol. Thus is should react much much faster with the tosylate.

[Caffeinated Chemist]

Well you are correct. You generate the phenoxide anion which is more nucleophillic than the phenol. Thus is should react much much faster with the tosylate.

Thank you very much!