1-Chloro-4-(chloromethyl)benzene → 1,3-Bis(4-chlorophenyl)-2,2-dimethylpropan-1-one

HRID 1380920Notes

Reaction equation

HRID 1380920 reaction equation
[CH:1]([C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5])([CH3:3])[CH3:2].[OH-].[K+].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][C:1]([C:4]([C:6]2[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=2)=[O:5])([CH3:3])[CH3:2])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium HydroxideHCID 728651-(4-Chlorophenyl)-2-methylpropan-1-one

Product 1

HCID 132174061,3-Bis(4-chlorophenyl)-2,2-dimethylpropan-1-oneYield 60%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

85 g (0.466 mol) of 4-chlorophenyl isopropyl ketone, 31.3 g (0.56 mol) of potassium hydroxide and 5 g of tetrabutylammonium bromide in 120 ml of toluene are heated to the reflux temperature, and a solution of 75 g (0.466 mol) of 4-chlorobenzyl chloride in 60 ml of toluene is added dropwise. The reaction mixture is subsequently stirred under reflux for 12 hours, cooled and washed with water and the organic phase is dried over sodium sulphate and concentrated in vacuo. 81.5 g (60% of theory) of 4-chlorophenyl 4-chlorophenyl-tert.-butyl ketone of refractive index nD20 1.5711 are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperaturecooled
  3. washwashed with water
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d860cf3ced7f43c4b635423a57a43aac
Source dataset
uspto-grants-1986_04
Patent number
US04584308

Reaction notes

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