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

Temperature

110 °C

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.

1. customResidue obtained
2. additionwas added
3. temperatureThe resulting mixture was heated
4. washThe ethyl acetate solution was washed with 5% hydrochloric acid
5. distillationdistilled water
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated

ORD record

ord-f93ed87b52ba42f0adc7607409623f30

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05486624