Example Ether TM

Synthesize the following TM, using only benzene and alcohol starting materials as sources of carbon (along with any necessary reagents that are conuner-cially available). 

The retrosynthesis begins by disconnecting the C-O bond that can be formed more easily, typically via an Sn2 mechanism. Since formation of the C-O bond at the aromatic ring would be more challenging, the disconnection shown is made instead to give a primary alkyl halide electrophile and a phenoxide nucleophile. Each of these compounds can be prepared from the corresponding alcohols, as required, and phenol can be synthesized from benzene via the phenyl diazonium salt. 

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