Hydrochloric Acid → Ethyl Ferulate

HRID 53834

Reaction equation

HRID 53834 reaction equation
[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)[CH3:16].Cl>CCCCCC.C(OCC)(=O)C>[C:1]([O:14][CH2:15][CH3:16])(=[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 445858Ferulic Acid

Product 1

HCID 736681Ethyl FerulateYield 85.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ferulic acid (4.85 g) and then ethyl alcohol (50 ml) containing hydrogen chloride (4%) were placed in an egg-plant type flask (200 ml), and heated under reflux for 2.5 hours. The disappearance of the starting material was confirmed by 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 wine-colored crude product (5.79 g). The resulting crude product was separated and purified by silica gel column chromatography (diameter=5.5×7.0 cm; 60 g; n-hexane/ethyl acetate=3/1) to obtain the above-identified compound (5.06 g; 91.2%). The product was crystallized from n-hexane to obtain a white crystal (4.743 g, 85.3%). Melting point: 41°-43° C.

Workup

  1. customwere placed in an egg-plant type flask
  2. temperature(200 ml), and heated
  3. temperatureunder reflux for 2.5 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 wine-colored crude product (5.79 g)
  8. customThe resulting crude product was separated
  9. custompurified by silica gel column chromatography (diameter=5.5×7.0 cm; 60 g; n-hexane/ethyl acetate=3/1)
  10. customto obtain the above-identified compound (5.06 g; 91.2%)
  11. customThe product was crystallized from n-hexane

Sources & evidence

ORD record
ord-7a97b72f08e548829656cc41b01ba99e
Source dataset
uspto-grants-1997_04
Patent number
US05621009

Linked notes

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