Reaktion #481605

ord-602d9d1954fa44eb829423fbca755f27

Reaktionsgleichung

COc1cc(C=O)cc(OC)c1O
3,5-Dimethoxy-4-hydroxy benzaldehyde
CCOC(=O)CC(C)=O
ethyl acetoacetate
O=C(O)CN1CCCCC1
piperidine—acetic acid
CCOC(=O)C(=Cc1cc(OC)c(O)c(OC)c1)C(C)=O
title product
CCOC(=O)C(=Cc1cc(OC)c(O)c(OC)c1)C(C)=O
Ethyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy-cinnamate

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturat reflux temperature

Vorschrift

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.

Quelle

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