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Benzophenone
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==Synthesis== Benzophenone is produced by the copper-catalyzed oxidation of [[diphenylmethane]] with air.<ref name="Ull">{{Ullmann|first1=Hardo |last1=Siegel |first2=Manfred |last2=Eggersdorfer |title=Ketones |doi=10.1002/14356007.a15_077}}</ref> A laboratory route involves the reaction of benzene with [[carbon tetrachloride]] followed by hydrolysis of the resulting [[diphenyldichloromethane]].<ref>{{OrgSynth | author = Marvel, C. S. |author2=Sperry, W. M. | title = Benzophenone | prep = cv1p0095 | collvol = 1 | collvolpages = 95 | year = 1941}}</ref> It can also be prepared by [[Friedel–Crafts acylation]] of [[benzene]] with [[benzoyl chloride]] in the presence of a [[Lewis acid]] (e.g. [[aluminium chloride]]) catalyst: since benzoyl chloride can itself be produced by the reaction of benzene with [[phosgene]] the first synthesis proceeded directly from those materials.<ref>{{cite journal |doi=10.1039/CA8783400019 |doi-access=free |title=Synthesis of benzoic acid and benzophenone |journal=Journal of the Chemical Society, Abstracts |year=1878 |volume=34 |pages=69–70 }}</ref> Another route of synthesis is through a palladium(II)/oxometalate catalyst. This converts an alcohol to a ketone with two groups on each side.<ref>{{cite journal|last1=Dornan |first1=L. |last2=Muldoon |first2=M. |title=A highly efficient palladium(II)/polyoxometalate catalyst system for aerobic oxidation of alcohols |journal=Catalysis Science & Technology |date=2015 |volume=5 |issue=3 |pages=1428–1432 |doi=10.1039/c4cy01632g}}</ref> Another, less well-known reaction to produce benzophenone is the [[pyrolysis]] of anhydrous calcium benzoate.<ref>{{cite journal|doi=10.1021/jo50015a003 | volume=18 | issue=9 | title=The Mechanism of the Ketonic Pyrolysis of Calcium Carboxylates | journal=The Journal of Organic Chemistry | pages=1079–1086 | last1 = Lee | first1 = C. C.| year=1953}}</ref>
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