Acetic Acid → 3-Acetoxy-2-cyclohexen-1-one

HRID 982857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982857
[OH:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.C(Cl)Cl.[C:12](O)(=[O:14])[CH3:13].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C.C(Cl)Cl.CC(C)=O>[O:8]=[C:4]1[CH2:5][CH2:6][CH2:7][C:2]([O:1][C:12](=[O:14])[CH3:13])=[CH:3]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 5357793-Hydroxycyclohex-2-enone

Produkt 1

HCID 27554433-Acetoxy-2-cyclohexen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 19841213hexane EtOAc CH2Cl2 acetoneLösungsmittel

Versuchsvorschrift

3-Hydroxy-cyclohex-2-enone (1.08 g, 9.64 mmol) was combined with methylene chloride (10 mL) in a 250 mL flask and acetic acid (1.4 eq, 13.75 mmol, 0.78 mL) was added to the mixture. The mixture was cooled in an ice bath and dicyclohexylcarbodiimide (1.3 eq, 12 mmol, 2.5 g) was added portionwise, followed by the addition of 4-(dimethylamino)pyridine (0.05 eq, 0.45 mmol, 50 mg). A sufficient amount of methylene chloride was added to ensure easy stirring and the reaction was monitored by TLC (silica gel, hexane-ethyl acetate-methylene chloride-acetone (3:3:3:1 v/v)), HPLC and LCMS and the intermediate acetic acid 3-oxo-cyclohex-1-enyl ester was formed. The mixture was stirred overnight at room temperature and then toluene (20 mL) was added. The mixture heated to 60° C. and after 72 hours the mixture was filtered, concentrated and purified by flash column chromatography to provide 2-acetyl-3-hydroxy-cyclohex-2-enone (1.19 g, 80%) as a colorless liquid. LCMS: MH+ 154.8.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath

Quellen und Nachweise

ORD-Eintrag
ord-95d84dee111c4b9abc2959d2e3c934f7
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861419B2

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