Hydrochloric Acid → Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

HRID 1861601

Reaktionsgleichung

Reaktionsgleichung von HRID 1861601
C[O-].[Na+].[CH3:4][C:5](=[CH2:9])[C:6](=[O:8])[CH3:7].[CH3:10][O:11][CH:12]([C:17]([O:19]C)=O)[C:13]([O:15][CH3:16])=[O:14].Cl>CS(C)=O>[OH:19][C:17]1[C:12]([O:11][CH3:10])([C:13]([O:15][CH3:16])=[O:14])[CH2:4][CH:5]([CH3:9])[C:6](=[O:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 13143Methyl isopropenyl ketoneHCID 78718Dimethyl methoxymalonateHCID 10942334Sodium Methoxide

Produkt 1

HCID 18755506Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A 30% solution of 35.8 g of sodium methoxide is introduced into 65 ml of dimethyl sulfoxide and, within 20 minutes, treated with a mixture of 16.7 g of 3-methyl-3-butene-2-one and 32.4 g of dimethyl methoxymalonate at a temperature of 30-35° C. The mixture is stirred for 1 hour at a temperature of 35° C., and is then acidified with hydrochloric acid and extracted repeatedly with dichloromethane. The organic phases are washed with water, dried and concentrated. Crystallization from hot ethyl acetate and hexane gives pure methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate of melting point 117-117.5° C.

Aufarbeitung

  1. extractionextracted repeatedly with dichloromethane
  2. washThe organic phases are washed with water
  3. customdried
  4. concentrationconcentrated
  5. customCrystallization from hot ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-24320ccc67c04b4f96aadf7909846525
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534445B1

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