4-Hydroxybenzaldehyde → P-Coumaric Acid

HRID 1604077Notes

Reaction equation

HRID 1604077 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[OH:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[CH:11][CH:10]=1.NC1C=CC=CC=1.Cl>N1C=CC=CC=1>[CH:11]1[C:12](/[CH:3]=[CH:2]/[C:1]([OH:7])=[O:6])=[CH:15][CH:16]=[C:9]([OH:8])[CH:10]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric Acid2×HCID 867Malonic AcidHCID 6115Aniline

Product 1

HCID 637542P-Coumaric AcidYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

Malonic acid, 813 g, was added to p-hydroxy benzaldehyde, 472 g, in pyridine, 957 ml. The mixture was heated to 65° C. and aniline, 28 ml, was added. The reaction was stirred at 65° C. for 7.5 hours and then cooled to room temperature. HCl, 2.75 L, 2N HCl, was then added dropwise while the reaction stirred A creamy precipitate formed. The reaction was stirred for an additional 10 minutes. The precipitate was collected by filtration and dried under reduced pressure. The solid was identified as coumaric acid by IR spectroscopy. The yield was ≥80%.

Workup

  1. temperaturecooled to room temperature
  2. stirringstirred A creamy precipitate
  3. customformed
  4. stirringThe reaction was stirred for an additional 10 minutes
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-cfff760b6e684307ae258b3caf98c6d2
Source dataset
uspto-grants-1999_11
Patent number
US05990336

Reaction notes

Loading…