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

HRID 1838633

Reaktionsgleichung

Reaktionsgleichung von HRID 1838633
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 dichioromethane. 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 dichioromethane
  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-14ea8c5fb8404035919e6ae11d1cddc9
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673938B1

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