Shriner, R. L. published the artcileThe structure of the nitration products of 9-phenylxanthylium salts, SDS of cas: 596-38-3, the publication is Journal of the American Chemical Society (1951), 891-4, database is CAplus.
cf. preceding abstract The nitration of 9-phenylxanthylium perchlorate (I) yielded 91% 9-(m-nitrophenyl)xanthylium perchlorate (II), as shown by hydrolysis to the carbinol (III) and reduction to 9-(m-nitrophenyl)xanthene (IV). The structure of IV was established by condensation of xanthydrol (V) with ο-O2NC6H4NH2 (VI) to 9-(4-amino-3-nitrophenyl)xanthene (VII) from which the NH2 group was removed by diazotization and H3PO2. These cationic salts orient the entering NO2 group to the m-position. Xanthone (VIIIa) and PhMgBr yielded 86% 9-phenylxanthydrol (VIII), m. 158-9° (Gomberg and Cone, C.A. 5, 90). HClO4 (5.85 g. 70%) added with stirring to 10 g. VIII in 50 cc. C6H6 and 25 cc. Me2CO, and the mixture refrigerated yielded 13.4 g. I, yellow crystals, m. 280-1° (explosive !). Excess FeCl3-HCl added to 2. g. VIII in HCl yielded 3.14 g. 9-phenylxanthylium ferrichloride, yellow crystals, m. 170°. Cold, concentrated HNO3 added during 5-10 min. to 10 g. VIII in 50 cc. concentrated H2SO4 (ice bath 5-10°), and the mixture poured onto 500 g. ice and neutralized with NH4OH, yielded 12 g. crude 9-(m-nitrophenyl)xanthydrol (IX), m. 55-9°. HClO4 (5 cc. 70%) added with stirring to 10 g. IX in 30 cc. 1:1 C6H6-Me2CO, and the mixture allowed to stand (cold) 24 h., yielded 11.3 g. II, yellow crystals from AcOH, m. 255-7° (corrected). Excess FeCl3-HCl added to 10 g. IX in a min. of concentrated HCl and chilled 24 h. at 5° yielded 13.6 g. 9-(m-nitrophenyl)xanthylium ferrichloride, orange crystals from AcOH, m. 242-3° (corrected). IX (2 g.) in 5 cc. concentrated H2SO4 added to 100 cc. MeOH, and the mixture allowed to stand at 20° 30 min. and poured onto 500 g. ice yielded 1.7 g. Me ether, white crystals from MeOH, m. 134-5°; Et ether, white prisms from EtOH, m. 118-19°. Na2CO3 (10 g.) added to 50 g. IX in 600 cc. 90% HCO2H, and the solution refluxed 1-1.5 h. and cooled 4 h. at 5-10° yielded 43.5 g. IV, pale tan crystals from EtOH, m. 155-6°. Cold, concentrated HNO3 (30 cc.) added during 5-10 min. (stirring) to 10 g. I in 40 cc. concentrated H2SO4, and the solution poured into ice water and neutralized with NH4OH yielded 11.2 g. crude nitrated carbinol, identical with IX. KMnO4 (50 g.) added with stirring and heating (steam bath) to 3 g. IX in 300 cc. water containing 60 cc. concentrated H2SO4, the mixture saturated with SO2, extracted with Et2O, and the Et2O removed, yielded 0.03 g. p-O2NC6H4CO2H, m. 240° when mixed with an authentic sample. Concentrated H2SO4 (140 cc.) added (stirring) to 300 cc. water containing 10 g. IX and 143 g. Na2Cr2O7, 55 cc. H2SO4 added dropwise during 30 min., and the mixture refluxed 2 h., cooled, filtered, and washed yielded 0.22 g. p- and 2.6 g. m-O2NC6H4CO2H. IV (2.0 g.) in 200 cc. absolute alc. reduced with Pt oxide 5-10 min. at 25° and 20 lb. pressure yielded 1.8 g. NH2 analog (X), white crystals, m. 154-5°. IV (1.0 g.) refluxed 8 h. with 10 cc. concentrated HCl, 15 cc. water, 15 cc. AcOH, and 2 g. Zn yielded 0.2 g. X, m. 153-5°. V (24 g.), 22 g. PhNH2, 6 cc. concentrated HCl, and 120 cc. AcOH refluxed 4 h., stirred into 2 l. cold water containing 20 g. Na2CO3, and the mixture stirred on the steam bath 30 min. and filtered hot yielded 34.5 g. of a mixture of 9-(p-aminophenyl)xanthene (XI) and its Ac derivative (XII). The solid refluxed 6 h. with 70 cc. concentrated HCl and 500 cc. 80% EtOH, cooled, poured into 2 l. cold water, neutralized with Na2CO3 and warmed on the steam bath 15-20 min. yielded 20 g. XI, white prisms from EtOH, m. 185°. XI (3 g.) refluxed 6 h. in 25 cc. AcOH and poured into water yielded 2 g. XII, white crystals from EtOH, m. 186-7°. VIIa (6.5 g.) in 30 cc. hot C6H6 added to p-MeOC6H4MgBr (from 1.2 g. Mg and 9.2 g. p-BrC6H4OMe) in 50 cc. Et2O, and the mixture stirred and refluxed 4 h. and hydrolyzed with NH4Cl yielded 6 g. 9-(p-methoxyphenyl)xanthydrol (XIII), white prisms from Me2CO, m. 120-1°. XIII (5 g.) in 100 cc. 90% HCO2H containing 2 g. Na2CO3 refluxed 1 h. yielded 4.3 g. 9-(p-methoxyphenyl)xanthene (XIV), white prisms from EtOH, m. 113-14°. NaNO2 (2.55 g.) added during 2 h. to 10 g. XI in 30 cc. AcOH and 10 cc. concentrated H2SO4, and the mixture poured into 50 cc. H2SO4 and 50 cc. water (boiling), boiled 15 min., and poured into ice water yielded 6 g. red solid, m. 130-40°, which, refluxed 20 h. with 0.8 g. NaOH, 3 cc. Me2SO4, and 20 cc. water, cooled, and poured into cold water, yielded 2.1 g. XIV, white prisms, m. 113-14° (from MeOH). V (24 g.), 20 g. VI, 10 cc. concentrated HCl, and 120 cc. AcOH refluxed 4 h., cooled to 25°, poured into 1 l. water containing 20 g. Na2CO3, and stirred on the steam bath 30 min., yielded 28 g. yellow solid, which, refluxed 8 h. with 400 cc. 80% EtOH and 100 cc. concentrated HCl, cooled, poured into 1 l. cold water, and treated with Na2CO3 yielded 17.8 g. VII, yellow crystals from 500 cc. absolute EtOH, m. 160-1°. VI (20 g.) added to 24 g. V in 450 cc. EtOH, 20 cc. AcOH added after solution, and the mixture stirred 2 h. at 25° and cooled 2 h. to 0-5° yielded 36.5 g. 9-(ο-nitrophenylamino)xanthene (XV), orange crystals from pyridine, m. 197-9° (uncorrected). XV (2 g.) refluxed 4 h. in 50 cc. 15% HCl and cooled to room temperature yielded 1.2 g. V, m. 116-20°, and 0.5 g. VI, m. 70-1°. V and AcNH2 in AcOH (Phillips and Pitt, C.A. 37, 5371.6) yielded N-xanthylacetamide, m. 237-9°. XV (10 g.) refluxed 4 h. in 50 cc. AcOH containing 2 cc. concentrated H2SO4, cooled to 25°, poured into 500 cc. water, 5 g. Na2CO3 added, and the mixture warmed on the steam bath 30 min. yielded 8.4 g. VII, m. 159-61° (from EtOH). NaNO2 (2.15 g.) in 10 cc. cold water added dropwise (15 min.) to 10 g. VII in 30 cc. AcOH and 5 cc. concentrated H2SO4 at 5°, the mixture stirred 1 h. at 5-10°, 15 cc. cold 50% H3PO2 added, the mixture stirred 1 h., kept at 0-5° 16 h., 10 cc. H3PO2 added, then 25 cc. water, the solution extracted with three 100-cc. portions of C6H6, the combined extracts washed with water, 20% NaOH, and water, and the C6H6 removed, yielded 8.1 g. red crystals, m. 120-30°, which, allowed to stand 8 h. at 25° in 125 cc. EtOH, yielded 0.5 g. IV, pale yellow crystals from EtOH, m. 155-6°.
Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C7H8BBrO3, SDS of cas: 596-38-3.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts