Benzoic acid, 3,5-dihydroxy-, ethyl ester → Ethyl 3-hydroxy-5-oxo-3-cyclohexene-1-carboxylate

HRID 229727

Reaktionsgleichung

Reaktionsgleichung von HRID 229727
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1)[CH3:2].C([O-])=O.[Na+]>C(O)C.[Pd]>[OH:12][C:7]1[CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH2:10][C:9](=[O:11])[CH:8]=1

Komponenten

5

Edukt 2

HCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl esterHCID 2723810Sodium Formate

Produkt 1

HCID 10559379Ethyl 3-hydroxy-5-oxo-3-cyclohexene-1-carboxylateAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

3,5-Dihydroxybenzoic acid ethyl ester (10 g, 54.89 mmol) was dissolved in ethanol (15 mL), followed by adding sodium formate (4.48 g, 65.87 mmol), replacing inside a reactor with nitrogen at 30° C. for 15 minutes, adding palladium on carbon (364 mg) and reacting at 30° C. for 3 hours then at 40° C. over night. Catalyst was filtered off, followed by neutralization with a 1N HCl solution, concentration under reduced pressure and purification of thus obtained residue with silica gel column chromatography (hexane/ethyl acetate=1/1 to 0/1) to obtain an objective compound (1.53 g, 15.1%).

Aufarbeitung

  1. waitreacting at 30° C. for 3 hours
  2. waitat 40° C. over night
  3. filtrationCatalyst was filtered off
  4. concentrationfollowed by neutralization with a 1N HCl solution, concentration under reduced pressure and purification of thus obtained residue with silica gel column chromatography (hexane/ethyl acetate=1/1 to 0/1)

Quellen und Nachweise

ORD-Eintrag
ord-1fb85f8cf26c47ed86e59354a3ca2edb
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563893B2

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