Sulfuric Acid → Ethyl 4-bromo-3-oxocyclohexanecarboxylate

HRID 1593613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593613
[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].OS(O)(=O)=O.C(O)(C)C>CC(C)=O.O>[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]1=[O:13]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 58999614HCID 58999614, Verbindung

Produkt 1

HCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-bromo-3-hydroxycyclohexanecarboxylate (15.06 g) in acetone (300 mL) at 0° C. was added CrO3 (12.0 g, 120 mmol), and 2 N H2SO4 (60 mL). The mixture was stirred at room temperature for 30 min. Isopropanol (15 mL) was added and the reaction was stirred for 20 min. The volume was reduced under vacuum then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc in hexane) afforded 6.7 g of tide compound.

Aufarbeitung

  1. stirringthe reaction was stirred for 20 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (10% EtOAc in hexane)
  7. customafforded 6.7 g of tide compound

Quellen und Nachweise

ORD-Eintrag
ord-1aa439f5d3704070b1ba649c12a848de
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297704B2

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