Reaction #481605

Reaction equation

3,5-Dimethoxy-4-hydroxy benzaldehyde

ethyl acetoacetate

piperidine—acetic acid

→

title product

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

Solvents

benzene

Conditions

Workup

1. 1
   Temperatureat reflux temperature

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.

Source