Reaktion #481600

ord-2c30a265a15946deb2c3af6cb2cd1968

Reaktionsgleichung

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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeat 40° C.
  2. 2
    Sonstigefor 8 hours

Vorschrift

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%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06602515B2uspto-grants-2003_08