Réaction #1135828

ord-c61766a74e0a4c0d948b92cb20e80cc8

Équation de réaction

COc1ccc(C2COc3c(ccc(OC(C)=O)c3C)C2=O)cc1OC
Acetic acid 3-(3,4-dimethoxy-phenyl)-8-methyl-4-oxo-chroman-7-yl ester
c1c[nH]cn1
imidazole
O
H2O
COc1ccc(C2COc3c(ccc(O)c3C)C2=O)cc1OC
3-(3,4-Dimethoxy-phenyl)-7-hydroxy-8-methyl-chroman-4-one

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONbefore pouring
  2. 2
    FiltrationA fine white precipitate was filtered off

Mode opératoire

Acetic acid 3-(3,4-dimethoxy-phenyl)-8-methyl-4-oxo-chroman-7-yl ester (1.1 g, 3.2 mmol) and imidazole (3.2 g, 47 mmol) were refluxed in EtOH (100 ml). The reaction was complete after 90 minutes and allowed to cool to room temperature before pouring into stirred H2O (800 ml). A fine white precipitate was filtered off and 1H NMR in d-CDCl3 indicated the solid was 3-(3,4-Dimethoxy-phenyl)-7-hydroxy-8-methyl-chroman-4-one in >95% purity (0.31 g, 30%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09381186B2uspto-grants-2016_07