Malonic Acid → Ferulic Acid

HRID 1611873Notes

Reaction equation

HRID 1611873 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>>[C:14]([OH:16])(=[O:15])/[CH:13]=[CH:2]/[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 1183Vanillin

Product 1

HCID 445858Ferulic Acid

Procedure

Ferulic acid is a compound contained, as an ester thereof, in natural substances, particularly plants such as rice and adlay and may be obtained as a purified product from such a plant or a synthesized product industrially obtained. A ferulic ester is obtained in a hydrous ethanol fraction after rice bran oil obtained from rice bran is partitioned with hydrous ethanol and hexane at room temperature under weakly alkaline conditions. Ferulic acid can be obtained by hydrolyzing the ferulic ester obtained by the above-described process with sulfuric acid with heating under pressure and purifying the resultant hydrolyzate or by culturing Pseudomonas in a medium containing clove oil from buds and leaves of Syzygium aromaticum MERRILL et PERRY, Myrtaceae by steam distillation, or eugenol obtained by purifying the clove oil and subjecting the medium to isolation and purification. When ferulic acid is prepared by chemical synthesis, it may be prepared by, for example, a condensation reaction of vanillin and malonic acid (Journal of American Chemical Society, 74, 5346, 1952).

Workup

  1. customobtained
  2. customby purifying the clove oil
  3. customto isolation and purification
  4. custommay be prepared by, for example

Sources & evidence

ORD record
ord-820f249bde174995991247ffba8d9963
Source dataset
uspto-grants-2006_01
Patent number
US06991812B2

Reaction notes

Loading…