4,4'-Dihydroxybenzophenone Explained

4,4′-Dihydroxybenzophenone is an organic compound with the formula (HOC₆H₄)₂CO. This off-white solid is a precursor to, or a degradation product of, diverse commercial materials. It is a potential endocrine disruptor.^[1]

Synthesis

4,4′-Dihydroxybenzophenone is prepared by the rearrangement of p-hydroxyphenylbenzoate:

HOC₆H₄CO₂C₆H₅ → (HOC₆H₄)₂CO

Alternatively, p-hydroxybenzoic acid can be converted to p-acetoxybenzoyl chloride. This acid chloride reacts with phenol to give, after deacetylation, 4,4′-dihydroxybenzophenone.

Uses

The main application of 4,4′-dihydroxybenzophenone is as a UV light stabilizer. It and its derivatives are found in cosmetics, plastics, films, adhesives and coatings, optical fiber, and printed circuit boards. It is the precursor to certain polycarbonate polymers.^[2]

References

1. Eddine . Ali Nasser . von Kries . Jens P. . Podust . Mikhail V. . Warrier . Thulasi . Kaufmann . Stefan H. E. . Podust . Larissa M. . 2008 . X-ray structure of 4,4′-dihydroxybenzophenone mimicking sterol substrate in the active site of sterol 14α-demethylase (CYP51) . doi . Journal of Biological Chemistry . 283 . 22 . 15152–15159 . 10.1074/jbc.M801145200 . 2397474 . 18367444 . free . 22025443 . free.
2. David Parker, Jan Bussink, Hendrik T. van de Grampe, Gary W. Wheatley, Ernst-Ulrich Dorf, Edgar Ostlinning, Klaus Reinking "Polymers, High-Temperature" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.