Water → Methyl 5-acetyl-2,4-dihydroxybenzoate

HRID 41378

Reaktionsgleichung

Reaktionsgleichung von HRID 41378
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].O>B(F)(F)F.CCOCC>[C:1]([C:16]1[C:17]([OH:19])=[CH:18][C:9]([OH:8])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 16523Methyl 2,4-Dihydroxybenzoate

Produkt 1

HCID 12482079Methyl 5-acetyl-2,4-dihydroxybenzoateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8000Boron trifluoride etherateLösungsmittel

Versuchsvorschrift

Acetic anhydride (3.06 g, 30.0 mmol) was added to methyl 2,4-dihydroxybenzoate (5.04 g, 30.0 mmol) in boron trifluoride diethyl etherate (7.6 ml) and the mixture was stirred and held at reflux for 3 hours and then allowed to cool to room temperature. Water (80 ml) was added and the mixture stirred at room temperature for 30 minutes. The resulting yellow solid was removed by filtration and sucked as dry as possible under vacuum. The solid was dissolved in dichloromethane and was washed with water, the organic layer was separated and the solvent removed in vacuo to afford methyl 5-acetyl-2,4-dihydroxybenzoate as a bright yellow solid (2.62 g, 42%) which was used without further purification. 1H NMR (DMSO-d6) 12.58 (1H, s), 11.22 (1H, s), 8.33 (1H, s), 6.45 (1H, s), 3.90 (3H, s), 2.62 (3H, s). MS: [M+H]+ 211.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. stirringthe mixture stirred at room temperature for 30 minutes
  3. customThe resulting yellow solid was removed by filtration
  4. customas dry as possible under vacuum
  5. dissolutionThe solid was dissolved in dichloromethane
  6. washwas washed with water
  7. customthe organic layer was separated
  8. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6fb595221e8b44d7a3546917a01c63ac
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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