Hydrochloric Acid → Butyl 3-(3,4-dihydroxyphenyl)acrylate

HRID 569636Notes

Reaction equation

HRID 569636 reaction equation
Cl.[C:2]([OH:14])(=[O:13])/[CH:3]=[CH:4]/[C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1>C(O)CCC>[CH2:2]([O:13][C:2](=[O:14])/[CH:3]=[CH:4]/[C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 689043Caffeic Acid

Product 1

HCID 9991705Butyl 3-(3,4-dihydroxyphenyl)acrylateYield 106.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 50 ml of butanol into which hydrogen chloride gas was introduced beforehand for about 10 minutes, was added 2 g of caffeic acid. The resulting mixture was heated at 90° to 100° C. and stirred for 3 hours. The reaction product was concentrated under a reduced pressure, and the residue obtained was purified by means of chromatography and then recrystallized from ether/hexane to give 1.4 g of caffeic acid butyl ester.

Workup

  1. temperatureThe resulting mixture was heated at 90° to 100° C.
  2. concentrationThe reaction product was concentrated under a reduced pressure
  3. customthe residue obtained
  4. customwas purified by means of chromatography
  5. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-e933a376915a455ab2dc58520e2a94f5
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

Loading…