Hydrochloric Acid → n-Propyl ferulate

HRID 53835

Reaction equation

HRID 53835 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)[CH2:16][CH3:17].Cl>CCCCCC.C(OCC)(=O)C>[C:1]([O:14][CH2:15][CH2:16][CH3:17])(=[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 10311-PropanolHCID 445858Ferulic Acid

Product 1

HCID 9881169n-Propyl ferulateYield 91.6%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ferulic acid (4.85 g) and then n-propyl alcohol (50 ml) containing hydrogen chloride (4%) were placed in an egg-plant type flask (200 ml), and heated under reflux overnight. 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=5.5×7.0 cm; 60 g; n-hexane/ethyl acetate=2/1) to obtain the above-identified compound (5.48 g, 91.6%) as colorless oil.

Workup

  1. customwere placed in an egg-plant type flask
  2. temperature(200 ml), and heated
  3. temperatureunder reflux overnight
  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=5.5×7.0 cm; 60 g; n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-5539af09cf30460d87b5b3f1018a439f
Source dataset
uspto-grants-1997_04
Patent number
US05621009

Linked notes

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