Isocrotonic acid
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| Density | 1.03 g·cm−3 [1] |
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| Template:Longitem | Crotonic acid (trans isomer) Angelic acid Senecioic acid |
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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 °C, it converts into crotonic acid. The compound can be prepared from 1,3Template:Nbhdibromo-[[2-Butanone|2Template:Nbhbutanone]] via the Favorskii rearrangement.[2]
Related compounds
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.[4]
- (Z)-(C6H5)CH=CHCH2COOH → α-naphthol + H2O
References
- ↑ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 894, Template:ISBN.
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