Piperonal → 3,4-Methylenedioxybenzylidenesuccinic acid

Dissolving 19.14 g of metal sodium in 400 ml of ethanol, 110.8 ml of diethyl succinate and 100 g of piperonal were added, and the solution was heated and refluxed for 3 hours. The reaction solution was concentrated in vacuo, and the residue was dissolved in 700 ml of water, and washed with 300 ml of diethyl ether. The water layer was stirred in ice, adjusted to pH 1 by concentrated hydrochloric acid, and extracted with 300 ml of diethyl ether. The diethyl ether layer was washed once with saturated brine, and dried over magnesium sulfate anhydride, and concentrated in vacuo. The obtained oily residue was dissolved by 181.4 g in 350 ml of ethanol, and 400 ml of 5N sodium hydroxide was added to stir overnight at room temperature. The reaction solution was concentrated in vacuo, and the residue was washed with 200 ml of diethyl ether. The water layer was stirred in ice, adjusted to pH 1 by concentrated hydrochloric acid, and extracted with 400 ml of ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate anhydride, and concentrated in vacuo. To the obtained residue, 300 ml of diethyl ether was added to solidify, and the captioned compound was obtained. Yield: 67.34 g.

1. additionwere added
2. temperaturethe solution was heated
3. temperaturerefluxed for 3 hours
4. concentrationThe reaction solution was concentrated in vacuo
5. dissolutionthe residue was dissolved in 700 ml of water
6. washwashed with 300 ml of diethyl ether
7. extractionextracted with 300 ml of diethyl ether
8. washThe diethyl ether layer was washed once with saturated brine
9. dry with materialdried over magnesium sulfate anhydride
10. concentrationconcentrated in vacuo
11. dissolutionThe obtained oily residue was dissolved by 181.4 g in 350 ml of ethanol
12. addition400 ml of 5N sodium hydroxide was added
13. stirringto stir overnight at room temperature
14. concentrationThe reaction solution was concentrated in vacuo
15. washthe residue was washed with 200 ml of diethyl ether
16. stirringThe water layer was stirred in ice
17. extractionextracted with 400 ml of ethyl acetate
18. washThe ethyl acetate layer was washed with saturated brine
19. dry with materialdried over magnesium sulfate anhydride
20. concentrationconcentrated in vacuo
21. additionTo the obtained residue, 300 ml of diethyl ether was added
22. customthe captioned compound was obtained

ORD 기록

ord-2c2c1f3c36c045219cd3364ec6cc4970

출처 데이터셋

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05594006