Ethyl bromoacetate → (2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester

HRID 38347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38347
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[CH:6][C:5]=1[OH:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CC(C)=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:13][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([O:10][CH3:11])=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])[CH3:26]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2515102-Isopropyl-4-methoxy-5-methyl-phenol

Produkt 1

HCID 59598614(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl esterAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 2-isopropyl-4-methoxy-5-methyl-phenol (3.933 g, 21.8 mmol) in acetone (100 ml) was added potassium carbonate (20 g, 145 mmol) and ethyl bromoacetate (5 ml, 45.1 mmol). The mixture refluxed over night and was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified with silica gel chromatography (10% to 15% methylene chloride in hexane) to yield (2-isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester as white solid (4.78 g, 82%).

Aufarbeitung

  1. temperatureThe mixture refluxed over night
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal
  8. customof drying agent
  9. concentrationthe organic solution was concentrated under reduced pressure
  10. customThe residue was purified with silica gel chromatography (10% to 15% methylene chloride in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1ca0a19f8fc24427b6f5b445feeff71b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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