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Benzyl Bromide → Methyl 1-benzyl-2-oxocyclopentane carboxylate

HRID 132762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 132762
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH3:16])=[O:14].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([C:9]1([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:11][CH2:12][C:8]1=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Produkt 1

HCID 10847172Methyl 1-benzyl-2-oxocyclopentane carboxylateAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

29.0 grams of anhydrous potassium carbonate and 132 ml of acetone were mixed, then with stirring, to the resulting mixture was dropwise added a solution of 13.0 ml of methyl 2-oxocyclopentane carboxylate in 66 ml of acetone. After stirring at room temperature for 30 minutes, 13.7 ml of benzyl bromide was dropwise added thereto, and the reaction was allowed to continue under reflux for 6 hours. Then the reaction mixture was cooled to room temperature, filtered, and concentrated, and 150 ml of toluene was added thereto. The resulting solution was washed with water (3×150 ml), dried over anhydrous sodium sulfate, concentrated, and distilled under reduced pressure. 13.4 g of colorless liquid as a distillate cut of 161-162° C./4.8 mmHg was collected. Yield: 55.1%.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 30 minutes
  2. temperatureunder reflux for 6 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. addition150 ml of toluene was added
  6. washThe resulting solution was washed with water (3×150 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. distillationdistilled under reduced pressure
  10. distillation13.4 g of colorless liquid as a distillate cut of 161-162° C./4.8 mmHg was collected

Quellen und Nachweise

ORD-Eintrag
ord-b93bbbc2655f4f9b84ab2c4ee57aeb80
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07388103B2

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