p-Xylyl bromide → HCID 12163287, Verbindung

HRID 132770

Reaktionsgleichung

Reaktionsgleichung von HRID 132770
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CC(C)=O>[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][C:3]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Produkt 1

HCID 12163287HCID 12163287, VerbindungAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Under vigorously agitation, 39.0 g of ethyl 2-oxocyclopentane carboxylate was added to 105.6 g (purity of 98%) of ground anhydrous potassium carbonate, and after stirring for several minutes, to the mixture was added 100 ml of acetone. The reaction mixture was further stirred for about 15 minutes, then thereto was dropwise added 34.35 ml (purity of 98%) of p-methylbenzyl bromide. Upon the completion of the addition, the reaction mixture was heated for reflux for 4 hours. The reaction mixture was filtered under the reduced pressure, and the filter cake was washed with diethyl ether until its color was purely white. Pale yellow filtrate was collected and dried over anhydrous magnesium sulfate, then the solvent was removed. The residue was distilled under reduced pressure, and 53.57 g of colorless liquid as a distillate cut of 144-146° C./100 Pa was collected. Yield: 82.4%. MS: m/e 260(M+′), 242, 232(M+′—CH2CH2), 215(M+′—OCH2CH3), 187(M+′—CO2CH2CH3), 171, 155(M+″—C8H9) 127, 105(base), 77.

Aufarbeitung

  1. stirringThe reaction mixture was further stirred for about 15 minutes
  2. additionUpon the completion of the addition
  3. temperaturethe reaction mixture was heated
  4. temperaturefor reflux for 4 hours
  5. filtrationThe reaction mixture was filtered under the reduced pressure
  6. washthe filter cake was washed with diethyl ether until its color
  7. customPale yellow filtrate was collected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. distillationThe residue was distilled under reduced pressure, and 53.57 g of colorless liquid as a distillate cut of 144-146° C./100 Pa
  11. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-9164a62fb99f48c1ac1ea99cbad8bc2b
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388103B2

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