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Isocrotonic acid

Isocrotonic acid (also known as quartenylic acid; formally named (Z)-2-butenoic acid) is the cis isomer of crotonic acid. It is an oil, possessing an odor similar to that of brown sugar. At its boiling point of 171.9 Ã‚°C, it converts into crotonic acid. The compound can be prepared from 1,3dibromo-2butanone via the Favorskii rearrangement.

Related compounds

Ethyl isocrotonate can be prepared by semihydrogenation of ethyl tetrolate.

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.

:(Z)-(C<sub>6</sub>H<sub>5</sub>)CH=CHCH<sub>2</sub>COOH &nbsp; → &nbsp; α-naphthol &nbsp; + &nbsp; H<sub>2</sub>O

References