3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → Methyl 4-hydroxy-3-methoxy-cinnamate

Reaktionsgleichung

[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14].S(=O)(=O)(O)O.[CH3:20]O>>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:20])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14]

Komponenten

Edukt 3

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid

HCID 887Methanol

HCID 1118Sulfuric Acid

Produkt 1

HCID 16830Methyl 4-hydroxy-3-methoxy-cinnamate

Versuchsvorschrift

The preparation was effected analogously to Example 1 from 25 g (0.129 mol) of 4-hydroxy-3-methoxy-cinnamic acid and 180 ml of methanol with concentrated sulphuric acid as the catalyst. For purification, it was chromatographed on silica gel with dichloromethane/diethyl ether (19:1). This gave 21.78 g of methyl 4-hydroxy-3-methoxy-cinnamate as a pale yellow oil.