Iodine → (1-Hydroxy-cyclohexyl)-acetic acid ethyl ester

HRID 1009922

Reaktionsgleichung

Reaktionsgleichung von HRID 1009922
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>C1COCC1.[Zn]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16]

Komponenten

7

Edukt 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 7967Cyclohexanone

Produkt 1

HCID 219250(1-Hydroxy-cyclohexyl)-acetic acid ethyl esterAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10% Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound (17.2 g, 94%) as a colorless oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c9ff6c360daa47fca2319dd9021b280f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973163B2

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