Water → Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate

HRID 228718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228718
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 23078435Methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoate

Produkt 1

HCID 23078392Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 8-(2-methoxy-5-methyl-phenyl)-8-oxo-octanoate (992 mg) was dissolved in methylene chloride (30 ml) to prepare a solution. 1 M boron tribromide (5.0 ml) was added at −78° C. to the solution, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate (271 mg, yield 29%).

Aufarbeitung

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d989e60f24574ba9a8b000e932ecdf71
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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