91Ó°ÊÓ

Benzyl phenyl ether is an organic ether that contains a phenyl group and benzyl group on either side of the oxygen atom. It is found in coals and is a reactive oxygenate. The IUPAC name of the compound is phenoxy methylbenzene.

The starting materials for the synthesis of benzyl phenyl ether are benzene and phenol.

Phenols are compounds in which one hydrogen atom of benzene is replaced with a hydroxyl group. The hydroxyl group in phenol has an acidic character. This is due to the resonance stabilization of the phenoxide ion formed by removing a proton from phenol. Therefore, phenols can be converted to phenoxides by reacting them with strong bases.

Benzene contains six equivalent hydrogen atoms. Benzene is an aromatic compound and therefore is highly stable. These hydrogen atoms can be replaced by alkyl or acyl groups in the presence of Lewis acids.

Step 1:

The step involves the synthesis of sodium phenoxide from phenol. The phenol reacts with a strong base like sodium hydride to eliminate hydrogen molecules. The phenoxide ion and sodium ion form the sodium phenoxide.

Synthesis of methoxy benzene

Step 2:

The benzene molecule undergoes Friedel-Crafts alkylation to form toluene. It involves the reaction of benzene with methyl chloride in the presence of Lewis acids like aluminium chloride to carry out substitution. The toluene formed reacts with N-bromosuccinimide in the presence of benzoyl peroxide to form benzyl chloride.

Synthesis of benzyl chloride

Step 3:

The sodium phenoxide formed from phenol and the benzyl chloride formed from benzene undergoes a condensation reaction eliminating sodium bromide to form benzyl phenyl ether.

Synthesis of benzyl phenyl ether