1-Chloro-4-(chloromethyl)benzene → 4-(4-Chlorophenyl)-3,3-dimethylbutan-2-one

HRID 1789064Notes

Reaction equation

HRID 1789064 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1.[CH:12]([C:15]([CH3:17])=[O:16])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][C:12]([CH3:14])([CH3:13])[C:15](=[O:16])[CH3:17])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 112513-Methyl-2-butanoneHCID 14797Potassium Hydroxide

Product 1

HCID 128706324-(4-Chlorophenyl)-3,3-dimethylbutan-2-oneYield 87%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

254.4 g (4 mols) of powdered technical grade potassium hydroxide (88% strength) are suspended in 1 liter of toluene, 40 g of tetrabutylammonium bromide are added, and a mixture of 644 g (4 mols) of 4-chlorobenzyl chloride and 430 g (5 mols) of methyl isopropyl ketone is then slowly added dropwise at 85° C. To complete the reaction, the mixture is stirred for a further 3 hours at 85° C. after the dropwise addition is complete. After the mixture has been cooled, the potassium chloride is filtered off and the filtrate is washed neutral. 732.5 g (87% of theory) of 1-(4-chlorophenyl)-2,2-dimethylbutan-3-one of boiling point 87°-90° C./0.05 mbar are obtained by fractional distillation.

Workup

  1. additionis then slowly added dropwise at 85° C
  2. customthe reaction
  3. additionafter the dropwise addition
  4. temperatureAfter the mixture has been cooled
  5. filtrationthe potassium chloride is filtered off
  6. washthe filtrate is washed neutral

Sources & evidence

ORD record
ord-b146a08d4e884b7fbc08bcc79a0d1f24
Source dataset
uspto-grants-1987_08
Patent number
US04686291

Reaction notes

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