Johnson-Claisen Rearrangement

Mechanism of the Johnson-Claisen Rearrangement

Original publication	J. Am. Chem. Soc.. 1970, 92, 741.
Reviews	Comp. Org. Syn.. 1991, 5, 827. Chem. Rev.. 2004, 104, 293. Chem. Rev.. 1988, 88, 1423.

Sample reactions

2,4,6-Trimethylbenzoic acid

125 °C, 3 h, 79%

AcOH

Hg(OAc)2, MeC(OMe)3

EtCO2H

Reflux, 18 h

MeC(OMe)3

Dean-Stark

EtCO2H

115 °C, 16 h, 50% (3 steps)

EtCO2H, n-PrC(OMe)3

145 °C, 3 h, 75%