Ferulic Acid → Calebin A

HRID 2201597Notes

Reaction equation

[C:1]([CH2:14]I)(=[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.[Na].[K].[C:18]([OH:31])(=[O:30])/[CH:19]=[CH:20]/[C:21]1[CH:29]=[CH:28][C:26]([OH:27])=[C:23]([O:24][CH3:25])[CH:22]=1>>[CH3:8][O:7][C:6]1[CH:5]=[C:4](/[CH:3]=[CH:2]/[C:1]([CH2:14][O:31][C:18](/[CH:19]=[CH:20]/[C:21]2[CH:29]=[CH:28][C:26]([OH:27])=[C:23]([O:24][CH3:25])[CH:22]=2)=[O:30])=[O:13])[CH:12]=[CH:11][C:9]=1[OH:10]

Participants

Reactant 4

HCID 445858Ferulic Acid

HCID 5360545Sodium

HCID 5462222Potassium

HCID 21583101HCID 21583101, compound

Product 1

HCID 637429Calebin A

Procedure

Calebin-A (10a) was prepared by reacting feruloyliodomethane with sodium or potassium salt of ferulic acid with reaction steps and conditions maintained as mentioned in the general synthetic scheme discussed herein above in Para 0010. The yield of the product was 60%.

Workup

customwith reaction steps and conditions
temperaturemaintained

Sources & evidence

ORD record: ord-61ccafda3e024bf19028de63b2135f74
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365486B2

Reaction notes

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