1-Chloro-4-nitrobenzene → p-(p-Nitrophenoxy)anisole

HRID 1577310Notes

Reaction equation

HRID 1577310 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[OH-].[K+]>O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 90154-MethoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 80637p-(p-Nitrophenoxy)anisoleYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 mole each of p-nitrochlorobenzene (79.0 g), p-hydroxyanisole (62.0 g), and potassium hydroxide (33.0 g, 86% pure), in 100 ml water was heated at 140° C. for about 3.5 hours. The resulting solid, collected by filtration, had a melting point of 100°-107° C. Reactants were further removed from the crude product by steam distillation, and the remaining solid was washed with copious amounts of water to afford a brown, granular mass of 4-methoxy-4'-nitrodiphenyl ether (83 g, 68% yield).

Workup

  1. filtrationThe resulting solid, collected by filtration
  2. customReactants were further removed from the crude product by steam distillation
  3. washthe remaining solid was washed with copious amounts of water

Sources & evidence

ORD record
ord-44e2180dd190439a9aa74e02ddac1598
Source dataset
uspto-grants-1981_09
Patent number
US04287372

Reaction notes

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