Reacción #481600

ord-2c30a265a15946deb2c3af6cb2cd1968

Ecuación de reacción

COc1cc(C=O)cc(OC)c1OC
3,4,5-trimethoxy benzaldehyde
O=S(=O)(O)O
sulphuric acid
COc1cc(C=O)cc(OC)c1O
3,5-Dimethoxy-4-hydroxy benzaldehyde

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroat 40° C.
  2. 2
    Otrofor 8 hours

Procedimiento

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%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06602515B2uspto-grants-2003_08