Isocrotonic acid

It is an oil, possessing an odor similar to that of brown sugar.

At its boiling point of 171.9 °C, it converts into crotonic acid.

The compound can be prepared from 1,3‑dibromo-2‑butanone via the Favorskii rearrangement.

[2] Ethyl isocrotonate can be prepared by semihydrogenation of ethyl tetrolate.

[3] Rudolph Fittig and Hugo Erdmann showed that the γ-phenyl structural analog of isocrotonic acid forms α-naphthol when dehydrated, an observation that provided useful evidence in understanding the nature of naphthalene.

Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model