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

HRID 1789064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789064
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b146a08d4e884b7fbc08bcc79a0d1f24
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04686291

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