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Methyl 3-phenylpropionate → Methyl 3-[4-(Phenylacetyl)phenyl]propionate

HRID 235193
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 235193
[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(=S)=S>[C:17]1([CH2:23][C:24]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:2][CH:3]=2)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7643Methyl 3-phenylpropionateHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 23353736Methyl 3-[4-(Phenylacetyl)phenyl]propionateAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g of methyl 3-phenylpropionate in 6 ml of carbon disulfide, 1.62 g of anhydrous aluminium chloride was added under ice-cooling, and then 0.94 g of phenylacetyl chloride was added dropwise and stirring was continued at room temperature for 6 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water, dried, and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1) to afford 1.05 g of colorless crystals. Recrystallization from isopropyl ether gave colorless flakes, mp 77°~78° C.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-11a2a227cbcd4406a8e9fbc603b6b55e
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05597848

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