Phenylacetyl chloride → HCID 10709050, Verbindung

HRID 235192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235192
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(=S)=S>[C:18]1([CH2:24][C:25]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:2][CH:3]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 281254Methyl 4-phenylbutyrateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 10709050HCID 10709050, VerbindungAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel2×

Versuchsvorschrift

To a solution of 25.0 g of methyl 4-phenylbutyrate in 100 ml of carbon disulfide, 37.3 g of anhydrous aluminium chloride was added and then a solution of 43.3 g of phenylacetyl chloride in 25 ml of carbon disulfide was added dropwise, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride layer was washed with aqueous potassium carbonate solution, dried, and then the solvent was removed. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1→methylene chloride) to afford 27.3 g of colorless crystals. Recrystallization from isopropyl ether gave colorless flakes, mp 54°~54.5° C.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride layer was washed with aqueous potassium carbonate solution
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1→methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-ffc49b6b7fb547d1ad87a90d1b605821
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597848

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