3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid → 2-(3,4-dihydroxycinnamoyl) oxymethyl-5-hydroxy-4H-pyran-4-one

HRID 375698

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[OH-].[Na+].CN(C)C=O.[CH:21]1[C:26](=[O:27])[C:25]([OH:28])=[CH:24][O:23][C:22]=1[CH2:29]Cl>CO.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([O:9][CH2:29][C:22]1[O:23][CH:24]=[C:25]([OH:28])[C:26](=[O:27])[CH:21]=1)=[O:8]

Participants

Conditions

Temperature: 110 °C

Procedure

0.81 g(4.5 mmol) of 3,4-dihydroxycinnamic acid and 0.18 g (4.5 mmol) of sodium hydroxide were dissolved into 40 ml of methanol. Residues obtained after distillating in methanol dissolved into 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 0.66 g(48.8%) of 2-(3,4-dihydroxycinnamoyl) oxymethyl-5-hydroxy-4H-pyran-4-one as a solid.

Workup

customResidues 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

Sources & evidence

ORD record: ord-968d7c5522eb4facb2fa62d9db9429ea
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486624

Linked notes

Loading…