3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid → Caffeic Acid

HRID 25331

Reaktionsgleichung

Reaktionsgleichung von HRID 25331
[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]>S(Cl)(Cl)=O>[C:7]([OH:9])(=[O:8])/[CH:6]=[CH:5]/[C:4]1[CH:10]=[CH:11][C:12]([OH:13])=[C:2]([OH:1])[CH:3]=1

Komponenten

3

Edukt 1

HCID 25183-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid

Produkt 1

HCID 689043Caffeic AcidAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3,4-Dihydroxycinnamic acid (1.13 g, 6.27 mmole) was dissolved in thionyl chloride (25 ml) and the solution was stirred for 5 hours at 40-60° C. The solvent was removed, the residue was dissolved in thoroughly dried ethyl acetate and the solution was slowly added to a solution of 5-methoxy tryptamine (1.2 g) in benzene, which contained also ethylamine (1 ml). The mixture was stirred overnight, water (10 ml) was added and the mixture again stirred for 15 minutes. The solvents were removed, the residue was dissolved in ethyl acetate and the solution was washed successively with water, saturated NaHCO3 solution, water and brine, and then dried over Na2SO4. The solvent was removed and the product was purified by column chromatography using 1:9 methanol/dichloromethane. The purification process was repeated three times to remove byproducts. The fraction identified as the caffeic acid 5-methoxytryptamide was further purified by recrystallization from ethyl acetate/hexane solution. The compound was obtained as white crystals (yield about 60%).

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in thoroughly dried ethyl acetate
  3. additionthe solution was slowly added to a solution of 5-methoxy tryptamine (1.2 g) in benzene, which
  4. stirringThe mixture was stirred overnight
  5. additionwater (10 ml) was added
  6. stirringthe mixture again stirred for 15 minutes
  7. customThe solvents were removed
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washthe solution was washed successively with water, saturated NaHCO3 solution, water and brine
  10. dry with materialdried over Na2SO4
  11. customThe solvent was removed
  12. customthe product was purified by column chromatography
  13. customto remove byproducts
  14. customwas further purified by recrystallization from ethyl acetate/hexane solution

Quellen und Nachweise

ORD-Eintrag
ord-ba6c13dc6def41ceab68579859c21fc9
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858642B1

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