Johnson-Claisen Rearrangement

Schematic representation of the Johnson-Claisen Rearrangement.
Mechanism of the Johnson-Claisen Rearrangement
Mechanism of the Johnson-Claisen Rearrangement
Sample reactions
intermediate structure intermediate structure
2,4,6-Trimethylbenzoic acid
125 °C, 3 h, 79%
intermediate structure
intermediate structure intermediate structure
AcOH
intermediate structure
intermediate structure
Hg(OAc)2, MeC(OMe)3
EtCO2H
Reflux, 18 h
intermediate structure
intermediate structure
MeC(OMe)3
Dean-Stark
EtCO2H
115 °C, 16 h, 50% (3 steps)
intermediate structure