Water → Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

HRID 988241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988241
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].[OH2:21]>CC(C)=O>[CH2:19]([O:18][C:15](=[O:17])[C:16]1[C:13]([CH3:12])=[CH:8][C:9]([O:21][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:10][C:1]=1[OH:4])[CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Produkt 1

HCID 14408138Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Ethyl-2,4-dihydroxy-6-methyl benzoate (4 g, 21 mmol) is dissolved in acetone (80 mL) and to this solution is added potassium carbonate (2.9 g, 21 mmol) and benzyl bromide (2.5 mL, 21 mmol). This mixture is heated at reflux for 16 hours. To the cooled reaction is added ethyl acetate (100 mL) and water (100 mL). The organic layer is washed with water (2×80 mL) and brine (2×80 mL), then dried over magnesium sulfate and the solvent removed in vacuo. The crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes) to give the title compound: 1H NMR (300 MHz, CDCl3) δ 7.38 (m, 5H), 6.41 (d, 1H), 6.38 (d, 1H), 5.05 (s, 2H), 4.40 (q, 2H), 2.51 (s, 3H), 1.40 (t, 3H).

Aufarbeitung

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 16 hours
  3. customTo the cooled reaction
  4. washThe organic layer is washed with water (2×80 mL) and brine (2×80 mL)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed in vacuo
  7. customThe crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-74f3fbcdfc8c403eb5466523a4df711a
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635655B1

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