Water → 2,6-Dihydroxybenzoic Acid Benzyl Ester

HRID 660612

Reaktionsgleichung

Reaktionsgleichung von HRID 660612
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(O)C>[CH2:14]([O:5][C:4](=[O:6])[C:3]1[C:2]([OH:1])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 93382,6-Dihydroxybenzoic AcidHCID 14798Sodium Hydroxide

Produkt 1

HCID 105863642,6-Dihydroxybenzoic Acid Benzyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dihydroxybenzoic acid (500 mg, 3.24 mmol) in ethanol (8 mL) is added NaOH (130 mg, 3.24 mmol). After the mixture is stirred at RT for 3 h, the solvent is removed under reduced pressure. The resulting sodium salt is dissolved in DMF (10 mL) then benzyl bromide (0.39 mL, 3.24 mmol) is added and the mixture is stirred at RT for 18 h. Water is added and the mixture is extracted with EtOAc. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (10:1) as eluent to give the title compound as an oil.

Aufarbeitung

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe resulting sodium salt is dissolved in DMF (10 mL)
  3. stirringthe mixture is stirred at RT for 18 h
  4. extractionthe mixture is extracted with EtOAc
  5. washThe organic phase is washed with water and brine
  6. dry with materialthen is dried over sodium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-115214700f544f67a14c86df45b5805b
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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