Water → 2-(4-Chlorophenoxy)-1-(4-chlorophenyl)-2-methylpropan-1-one

HRID 1380923Notes

Reaction equation

HRID 1380923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25](Br)([CH3:27])[CH3:26])=[O:24])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:25]([C:23]([C:20]2[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][CH:21]=2)=[O:24])([CH3:27])[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 112999732-Bromo-1-(4-chlorophenyl)-2-methylpropan-1-one

Product 1

HCID 198424902-(4-Chlorophenoxy)-1-(4-chlorophenyl)-2-methylpropan-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

52 g (0.3982 mol) of p-chlorophenol and 55 g (0.3982 mol) of potassium carbonate in 400 ml of toluene are heated under reflux for 2 hours, using a water separator. The mixture is cooled to 40° C. and a solution of 2-bromo-prop-2-yl 4-chlorophenyl ketone in 170 ml of toluene is added dropwise. This reaction mixture is subsequently stirred at 100° C. for 5 hours and is then cooled, water is added and the organic phase is separated off. This phase is washed with dilute sodium hydroxide solution and water, dried over sodium sulphate and concentrated. 87 g (85% of theory) of crude 4-chlorophenyl 2-(p-chlorophenoxy)-prop-2-yl ketone are obtained and are further reacted directly. ##STR160##

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureis then cooled
  3. customthe organic phase is separated off
  4. washThis phase is washed with dilute sodium hydroxide solution and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fcef4b0198d04eddb2296940c5f41692
Source dataset
uspto-grants-1986_04
Patent number
US04584308

Reaction notes

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