Hydrochloric Acid → Ethyl (1-hydroxy-3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetate

HRID 420250

Reaktionsgleichung

Reaktionsgleichung von HRID 420250
Br[Zn][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:9][C:10]1[C:11](=[O:18])[C:12]([CH3:17])=[CH:13][C:14](=[O:16])[CH:15]=1.Cl.C(OCC)(=O)C>C1COCC1>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:14]1([OH:16])[CH:13]=[C:12]([CH3:17])[C:11](=[O:18])[C:10]([CH3:9])=[CH:15]1)[CH3:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 682412,6-Dimethyl-1,4-benzoquinoneHCID 178472539HCID 178472539, Verbindung

Produkt 1

HCID 326863Ethyl (1-hydroxy-3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under nitrogen atmosphere, 6 mL of. THF was added to 1.22 g (2 mmol, 0.6 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 0.45 g (3.33 mmol) of 2,6-dimethyl-p-benzoquinone in 3 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 1 hour. 5 mL of 1N hydrochloric acid was added dropwise at 20° C. or lower, followed by dilution with 25 mL of ethyl acetate. Then, the layers were separated. The organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 10 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution. After washing, the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3) afforded 0.60 g of the desired product (yield 80%).

Aufarbeitung

  1. stirringThe mixture was stirred at 20˜25° C. for 1 hour
  2. customThen, the layers were separated
  3. washThe organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 10 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution
  4. washAfter washing
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationAfter concentration
  7. customunder reduced pressure, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-f1e4af8260da4eb289836e2bbb3c2a02
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093403B2

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