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Boron tribromide → 4-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

HRID 1798100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1798100
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[O:17]C)=[O:7].B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[OH:17])=[O:7].[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[OH:17])=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 25134Boron tribromideHCID 582925834-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

Produkt 2

HCID 582926554-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl esterAusbeute 34 %HCID 582928314-(2-Hydroxy-4-methoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl esterAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 4-(2,4-dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (1.0 g, 3.76 mmol) in dichloromethane (10 mL) was added 1 M BBr3 in dichloromethane (15.04 mL). The reaction mixture was stirred at room temperature for 48 hours then poured onto ice and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was dissolved in concentrated H2SO4 (0.2 mL) and MeOH (10 mL) and the mixture was heated at 75° C. for 1 hour. The mixture was concentrated in vacuo and the residue was purified by silica gel flash column chromatography to give 4-(2-hydroxy-4-methoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (0.300 g, 31%) and 4-(2,4-dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (0.300 g, 34%).

Aufarbeitung

  1. additionthen poured onto ice
  2. extractionextracted with EtOAc
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in concentrated H2SO4 (0.2 mL)
  6. temperatureMeOH (10 mL) and the mixture was heated at 75° C. for 1 hour
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c072c1aa52c5411d8b0da9af936fa858
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343944B2

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