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

HRID 1674458Notes

Reaction equation

HRID 1674458 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-4c1f413e2a77400a9530d17a297c7843
Source dataset
uspto-grants-2011_08
Patent number
US08003082B2

Reaction notes

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