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XANTHONE (dibenzo-y-pyrone, or diphen...

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Originally appearing in Volume V28, Page 882 of the 1911 Encyclopedia Britannica.
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XANTHONE (dibenzo-y-pyrone, or diphenylene ketone See also:oxide)  , C13HiO2, in organic See also:chemistry, a heterocyclic See also:compound containing the See also:ring See also:system shown below . It is obtained by the oxidation of xanthene (methylene diphenylene See also:oxide) with chromic See also:acid; by the See also:action of See also:phosphorus oxycliloride on disodium salicylate; by See also:heating 2.2'-dioxybenzophenone with concentrated sulphuric acid; by distilling fluoran with See also:lime; by the oxidation of xanthydrol (R . See also:Meyer, Ber., 1893, 26, p . 1277); by boiling diazotized 2.2'-diaininobenzophenone with See also:water (Heyl., Ber., 1898, 31, p . 3034) ; by heating salol with concentrated sulphuric acid (C . Graebe, See also:Ann., 1889, 254, p . 280), and by heating See also:potassium-ortho=chlorobenzoate with See also:sodium phenolate and a small quantity of See also:copper See also:powder to 180–190° C . (F . See also:Ullmann, Ber., 1905, 38, pp . 729, 2120, 2211) . It crystallizes in needles which melt at 173–174° and See also:boil at 349–350° C., and are volatile in See also:steam . Its See also:solution in concentrated sulphuric acid is of a yellow See also:colour and shows a marked See also:blue See also:fluorescence .

The carbonyl See also:

group is not ketonic in See also:character since it yields neither an oxime nor See also:hydrazone . When fused with See also:caustic potash it yields phenol and salicylic acid . Mild reducing agents convert it into xanthydrol, the group > CO becoming > CH•OH, whilst a strong reducing See also:agent like hydriodic acid converts it into xanthene, the group> CO becoming> See also:CH2 . Phosphorus pentasulphide at 140–150° C. converts it into xanthion by transformation of > CO to >CS (R . Meyer, Ber., 1900, 33, p . 2580), and this latter compound condenses with See also:hydroxylamine to See also:form See also:xanthone oxime . All four mono-hydroxyxanthones are known, and are prepared by heating salicylic acid with either See also:resorcin, See also:pyrocatechin or hydroquinone; they are yellow crystalline solids, which See also:act as dyestuffs . The 1.7-di,hydroxyxanthone, known as euxanthone, is prepared by heating euxanthic acid with hydrochloric acid or by heating hydrouinone carboxylic acid with l3-resorcylic acid and acetic anhydride (S . Kostanecki, Ber., 1891, 24, p . 3983E C . Graebe, Ann., 1889, 254, p . 298) .

It is also obtained from See also:

Indian yellow (Graebe, ibid.), formed in the urine of cows fed on See also:mango leaves . It crystallizes in yellow needles which See also:sublime readily . On See also:fusion with caustic potash it decomposes with formation of tetrahydroxy-See also:benzophenone, which then breaks up into resorcin and hydroquinone . The isomeric 1.6-dihydroxyxanthone, isoeuxanthone, is formed when 13-resorcylic acid is heated with acetic anhydride . Gentisein, or 1.3.7-trihydroxyxanthone, is found in the form of its methyl See also:ether (gentisin) in See also:gentian See also:root; it is obtained synthetically by condensing phloroglucin with hydroquinone carboxylic acid . Xanthene, C15H1oO, may be synthesized by condensing phenol with ortho-cresol in the presence of See also:aluminium chloride . Its tetramethyl-diamino derivative, which is formed by condensing formaldehyde with dimethyl-See also:meta-aminophenol and subsequent elimination of water from the resulting See also:diphenyl methane derivative, is the leuco See also:base of pyronine, into which it passes by oxidation . Cl(CHa)2N/\/\ o /\% 8 7/\/CO\, /~//CH\ \/\ /\/~3 5 4 Xanthone . Pyronine .

End of Article: XANTHONE (dibenzo-y-pyrone, or diphenylene ketone oxide)
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