4-Chlorophenol → 1-Chloro-4-(4-methoxyphenoxy)benzene

HRID 263074Notes

Reaction equation

HRID 263074 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[K+].Br[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>C(OCC)C.[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 77304-BromoanisoleHCID 14797Potassium Hydroxide

Product 1

HCID 101054561-Chloro-4-(4-methoxyphenoxy)benzene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 67 g (0.520 mol) of p-chlorophenol and 29.5 g (0.520 mol) of KOH pellets is heated to 100° C. for 2 hours under a pressure of about 5 mm Hg. Thereafter 117 g (0.625 mol) of p-bromoanisole and 1 g of copper powder are added and the mixture is then heated to about 220°-230° C. for 5 hours. The cooled reaction mixture is taken up in diethyl ether and after removing the inorganic salts by filtration the filtrate is washed with 2 N sodium hydroxide solution and with water. The solvent is driven off under reduced pressure, drying is carried out with sodium sulphate and 133 g of an orange-coloured oil are obtained. Purification of this oil by distillation under reduced pressure given 70 g of a white crystalline mass which is insoluble in water.

Workup

  1. temperaturethe mixture is then heated to about 220°-230° C. for 5 hours
  2. customThe cooled reaction mixture
  3. customafter removing the inorganic salts
  4. filtrationby filtration the filtrate
  5. washis washed with 2 N sodium hydroxide solution and with water
  6. customdrying
  7. customare obtained
  8. customPurification of this oil
  9. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-ced8447b571f406596cb29ca5694b30e
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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