Water → Methyl 2-hydroxy-4-octyloxybenzoate

HRID 742524

Reaktionsgleichung

Reaktionsgleichung von HRID 742524
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CC(=O)CC>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Produkt 1

HCID 11536459Methyl 2-hydroxy-4-octyloxybenzoateAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a solution of 33.0 g (196 mmol) of methyl 2,4-dihydroxybenzoate and 68.0 g (491 mmol) of potassium carbonate mixed in 500 ml of 2-butanone was added 50 ml (235 mmol) of octyl bromide and the whole was refluxed for 18 hours. Water was added to the solution and the whole was extracted with ethyl acetate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 40.4 g of methyl 2-hydroxy-4-octyloxybenzoate (29) as a colorless clear liquid (yield: 73.5%).

Aufarbeitung

  1. temperaturethe whole was refluxed for 18 hours
  2. extractionthe whole was extracted with ethyl acetate
  3. customAfter removal of the solvent
  4. distillationby distillation
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-776baa8f937f44c7ade1ce37e348ab2f
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554706

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