Reaction #481600

Reaction equation

3,4,5-trimethoxy benzaldehyde

sulphuric acid

→

3,5-Dimethoxy-4-hydroxy benzaldehyde

Conditions

Workup

1. 1
   Otherat 40° C.
2. 2
   Otherfor 8 hours

Procedure

Monodemethylation of 3,4,5-trimethoxy benzaldehyde using sulphuric acid at 40° C. for 8 hours yields 3,5-Dimethoxy-4-hydroxy benzaldehyde (Syringaldehyde). Condensation of syringaldehyde with ethyl cyanoacetate in the presence of piperidine—acetic acid and benzene as the reaction medium at reflux temperature under continuous azeotropic water removal yields the title product. The reaction takes about 1.5 hours for completion. The yield obtained is typically 95%.

Source