1-Butanol → Butyl 4'-hydroxy-3'-methoxycinnamate

HRID 53836

Reaktionsgleichung

Reaktionsgleichung von HRID 53836
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[CH2:15](O)[CH2:16][CH2:17][CH3:18].Cl>CCCCCC.C(OCC)(=O)C>[C:1]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1

Komponenten

5

Edukt 3

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 445858Ferulic Acid

Produkt 1

HCID 6437331Butyl 4'-hydroxy-3'-methoxycinnamateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Ferulic acid (5 g) and then n-butyl alcohol (50 ml) containing hydrogen chloride (4%) were placed in an egg-plant type flask (200 ml), and heated under reflux for about 2 hours. The disappearance of the starting material was confirmed by thin layer chromatography (TLC: n-hexane/ethyl acetate=2/1), then the solvent was evaporated under reduced pressure by a rotary evaporator. Benzene was added to the residue, and then, the solvent was again evaporated by a rotary evaporator to obtain the crude product. The resulting crude product was separated and purified by silica gel column chromatography (diameter=5.5×8.5 cm; 70 g; n-hexane/ethyl acetate=2/1) to obtain the above-identified compound (6.25 g, 99%) as colorless oil.

Aufarbeitung

  1. customwere placed in an egg-plant type flask
  2. temperature(200 ml), and heated
  3. temperatureunder reflux for about 2 hours
  4. customthe solvent was evaporated under reduced pressure by a rotary evaporator
  5. additionBenzene was added to the residue
  6. customthe solvent was again evaporated by a rotary evaporator
  7. customto obtain the crude product
  8. customThe resulting crude product was separated
  9. custompurified by silica gel column chromatography (diameter=5.5×8.5 cm; 70 g; n-hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-cc19e1472d3745c78b697defa40b20bd
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621009

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