4-Hydroxybenzaldehyde → Licochalcone A

HRID 394962Notes

Reaction equation

HRID 394962 reaction equation
CO[C:3]1[CH:10]=[C:9]([O:11]CC=C(C)C)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:17][O:18][C:19]1[CH:26]=[C:25]([OH:27])[C:24]([C:28]([CH3:32])([CH3:31])[CH:29]=[CH2:30])=[CH:23][C:20]=1[CH:21]=O.O[C:34]1C=CC(C=O)=CC=1>>[CH3:31][C:28]([C:24]1[CH:23]=[C:20](/[CH:21]=[CH:34]/[C:5]([C:4]2[CH:3]=[CH:10][C:9]([OH:11])=[CH:8][CH:7]=2)=[O:6])[C:19]([O:18][CH3:17])=[CH:26][C:25]=1[OH:27])([CH:29]=[CH2:30])[CH3:32]

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 110853192-Methoxy-4-[(3-methyl-2-buten-1-yl)oxy]benzaldehydeHCID 12153345HCID 12153345, compound

Product 1

HCID 5318998Licochalcone A

Procedure

The Claisen rearrangement of 2-methoxy-4-(3-methylbut-2-enyloxy)benzaldehyde and the Claisen condensation of the resulting 2-methoxy-4-hydroxy-5-(1,1-dimethyl-prop-2-enyl)benzaldehyde with 4-hydroxybenzaldehyde to give licochalcone A was performed according to the Chinese procedure:

Sources & evidence

ORD record
ord-d16904f34e714591989e32f92309d3f8
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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