3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → 2-(4-hydroxy-3-methoxy cinnamoyl)oxymethyl-5-hydroxy-4H-pyran-4-one

HRID 375699

Reaktionsgleichung

[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14].[OH-].[Na+].CO.[CH:19]1[C:24](=[O:25])[C:23]([OH:26])=[CH:22][O:21][C:20]=1[CH2:27]Cl>CN(C)C=O.C(OCC)(=O)C>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:27][C:20]2[O:21][CH:22]=[C:23]([OH:26])[C:24](=[O:25])[CH:19]=2)=[O:9])=[CH:4][C:3]=1[O:13][CH3:14]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

0.87 g(4.5 mmol) of 4-hydroxy-3-methoxycinnamic acid and 0.18 g(4.5 mmol) of sodium hydroxide were dissolved into 40 ml of methanol. Residue obtained after distillating methanol was dissolved in 70 ml of N,N-dimethylformamide and 0.65 g (4.05 mmol) of chlorokojic acid prepared in the Reference Example was added thereto. The resulting mixture was heated with stirring for 2 hours in an oil bath of 110° C. After distillating the solvent, the residue was dissolved in 300 ml of ethyl acetate. The ethyl acetate solution was washed with 5% hydrochloric acid and distilled water, dried over magnesium sulfate, decolored with active charcoal and filtered. The filtrate was concentrated to give 0.6g(41.9%) of 2-(4-hydroxy-3-methoxy cinnamoyl)oxymethyl-5-hydroxy-4H-pyran-4-one as a solid.

Aufarbeitung

customResidue obtained
additionwas added
temperatureThe resulting mixture was heated
washThe ethyl acetate solution was washed with 5% hydrochloric acid
distillationdistilled water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-f93ed87b52ba42f0adc7607409623f30
Quelldatensatz: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05486624

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