Syringaldehyde → HCID 54431732, compound

HRID 394423Notes

Reaction equation

HRID 394423 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 54431732HCID 54431732, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Monodemethylation of 3,4,5-trimethoxy benzaldehyde using sulphuric acid at 40° C. for 8 hours as described above in Example 1 yields syringaldehyde. 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-602d9d1954fa44eb829423fbca755f27
Source dataset
uspto-grants-2003_08
Patent number
US06602515B2

Reaction notes

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