Pyridine → 3-Acetoxy-2-cyclohexen-1-one

HRID 2366498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366498
[C:1](Cl)(=[O:3])[CH3:2].[C:5]1(=[O:12])[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([O:11][C:7]1[CH2:8][CH2:9][CH2:10][C:5](=[O:12])[CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 104341,3-Cyclohexanedione

Produkt 1

HCID 27554433-Acetoxy-2-cyclohexen-1-oneAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

According to Scheme 4 Step 1: Acetyl chloride (19.6 mmol, 1.39 mL) was added to a solution of cyclohexane-1,3-dione (17.8 mmol, 2.00 g) and pyridine (17.8 mmol, 1.28 mL) in CHCl3 (60 mL) and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with the addition of water and the organic phase was washed with a solution of HCl (0.1 M, 30 mL), a saturated solution of NaHCO3 (30 mL) and water (30 mL). The organic phase was dried over Na2SO4 and concentrated to yield 3-oxocyclohex-1-enyl acetate (13.2 mmol, 2.04 g, 74%) as a yellow oil.

Aufarbeitung

  1. customThe reaction was quenched with the addition of water
  2. washthe organic phase was washed with a solution of HCl (0.1 M, 30 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-02407e83c87e41628812d8e79f688099
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697744B2

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