Syringaldehyde → Ethyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy-cinnamate

HRID 1374489Notes

Reaction equation

HRID 1374489 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17].N1(CC(O)=O)CCCCC1>C1C=CC=CC=1>[CH2:21]([O:20][C:14](=[O:19])[C:15]([C:16](=[O:17])[CH3:18])=[CH:6][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=1)[CH3:22]

Participants

5

Reactant 3

HCID 8655SyringaldehydeHCID 8868Ethyl AcetoacetateHCID 201097Piperidin-1-yl-acetic acid

Product 1

HCID 54431732Ethyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy-cinnamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Condensation of 3,5-Dimethoxy-4-hydroxy benzaldehyde (syringaldehyde) with ethyl acetoacetate in the presence of piperidine-acetic acid and benzene as the reaction medium at reflux temperature yields the title product. The reaction takes about 3.5 hours for completion.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-8fcc5cfecdda4a91b87bd31d63eb0661
Source dataset
uspto-grants-2007_01
Patent number
US07166273B2

Reaction notes

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