Phenol → 2-Chlorodiphenyl ether

HRID 1492044Notes

Reaction equation

HRID 1492044 reaction equation
[OH-].[K+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1Cl>O.[Cu]I>[CH:6]1[CH:7]=[CH:8][C:3]([O:9][C:12]2[C:11]([Cl:10])=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 72391,2-DichlorobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 759002-Chlorodiphenyl etherYield 56.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

85% Potassium hydroxide powders (2.18 g; 0.033 mol, 1.1 equimolar amount) were added to phenol (4.23 g; 0.045 mol, 1.5 eq.) under heating, and 1,2-dichlorobenzene (4.41 g; 0.03 mol) and copper(I) iodide (0.29 g; 0.0015 mol) were added thereto, followed by stirring at 160° C. for 24 hours. The reaction mixture was diluted with water and extracted with ether. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with a mixture of benzene and n-hexane to give 3.48 g (yield, 56.7%) of 2-chlorodiphenyl ether as colorless crystals. m.p., 33° to 41° C.

Workup

  1. temperatureunder heating
  2. extractionextracted with ether
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography with a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-c6d7bc13027a4171b18fc9457ded11b1
Source dataset
uspto-grants-1994_12
Patent number
US05371223

Reaction notes

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