Outline a reasonable synthesis of 4-nitrophenyl phenyl ether from chlorobenzene and phenol.

The mechanism of the formation of 4-nitrophenyl phenyl ether include the electrophilic substitution in phenol and the nitration of chlorobenzene.

Explanation:

To prepare the 4-nitrophenyl phenyl ether appropriate equivalent of aqueos NaOH is added to absolute phenol, dissolved gives a Phenoxide ion aqueous and is then added.

After the addition of the appropriate mole of  chlorobenzene, to the mixture of HNO3 and H2SO4 is heated under reflux with stirring and exclusion of moisture for 5 hours. The alcohol is distilled off from the reaction mixture to a substantial extent through a 20-cm Vigreux column with stirring and the cooled distillation residue is poured into 100 ml of 5% caustic sodium carbonate; the organic phase is extracted several times with diethyl ether, washed with water, and dried with calcium chloride; the solvent is distilled off, and the residue is fractionated or recrystallized from ethanol. Unchanged phenol can be recovered by acidifying the aqueous alkaline solution and extracting it with ether.

The yield of 4-nitrophenyl phenyl ether 80%, m.p. 40°C; b.p. 286-287 °C; in the presence of HNO3 and H2SO4