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4-Isopropenylphenol is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula . The molecule consists of a 2-propenyl group (CH2=''C''-CH3) affixed to the 4 position of
phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
. The compound is an intermediate in the production of
bisphenol A Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial s ...
(BPA), 2.7 Mkg/y of which are produced annually (2007). It is also generated by the recycling of ''o,p''-BPA, a byproduct of the production of the ''p,p''-isomer of BPA.


Synthesis and reactions

The high-temperature hydrolysis of BPA gives the title compound together with phenol: : The compound can also be produced by catalytic dehydrogenation of 4-isopropylphenol. 4-Isopropenylphenol undergoes ''O''-protonation by
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
, giving the
carbocation A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountere ...
, which undergoes a variety of dimerization reactions.


References

{{DEFAULTSORT:Isopropenylphenol, p- Phenols Commodity chemicals Isopropenyl compounds