Hydrochloric Acid → Methyl 5-(4-chlorophenyl)-5-oxovalerate

HRID 264777

Reaktionsgleichung

Reaktionsgleichung von HRID 264777
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl[C:13]([CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:14].Cl>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:14])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 73916Methyl 4-chloroformylbutyrateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 10966649Methyl 5-(4-chlorophenyl)-5-oxovalerateAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Chlorobenzene (8.13 ml, 79.9 mmol) was dissolved in 100 ml of 1,2-dichloroethane, and 21.3 g (160 mmol) of aluminum trichloride and 12.15 ml (87.9 mmol) of methyl 4-(chloroformyl)butyrate were added thereto, followed by stirring the mixture at room temperature overnight. The reaction solution was poured into hydrochloric acid, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica-gel column chromatography (eluent: a mixture of 4% ethyl acetate and hexane) to obtain 15.8 g of the above-mentioned compound (yield 82%).

Aufarbeitung

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe resulting residue was purified by silica-gel column chromatography (eluent
  5. additiona mixture of 4% ethyl acetate and hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3f0f68dd45e943b8a27883536a64ad75
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646283

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