Reactions with halogen-substituted xanthones. II was written by Mustafa, Ahmed;Asker, Wafia;Sobhy, Mohamed Ezz El-Din. And the article was included in Journal of the American Chemical Society in 1955.Product Details of 100927-02-4 The following contents are mentioned in the article:
The reduction of halogen-substituted xanthones with LiAlH4 and with metallic Na and EtOH led to the formation of xanthene (I) with loss of the halogen. The reduction of xanthone (II) to I with LiAlH4 is discussed. 1-Chloro-(III), 1-6-dichloro-4-methylxanthone (IV), and 1-chloro-4-methylthiaxanthone (V) condense with aromatic thiols in the presence of KOH to yield the corresponding arylmercapto derivatives which are oxidized readily to the corresponding sulfone derivatives Whereas 2-chloroxanthone (VI) undergoes a photochem. addition reaction with I in sunlight to give the carbinol VII, the 4-isomer (VIII) of VI effects the photochem. dehydrogenation of I to 9,9′-bixanthene (IX). 2-Chloro-9-phenylxanthone (X) undergoes a photochem. oxidation in sunlight in the presence of O, yielding the peroxide (XI) of X. VI (1 g.) in 30 cc. C6H6 added in portions to 0.7 g. LiAlH4 in 50 cc. Et2O, the mixture refluxed 3 h., kept at room temperature overnight, and treated with cold dilute HCl, the Et2O layer worked up, and the solid residue washed with about 40 cc. petr. ether and recrystallized from MeOH gave almost quant. I. The 4-isomer (XII) and the 2-Br (XIII) and 4-Br (XIV) analogs of VI gave identical results. III (1 g.) treated with LiAlH4 in the usual manner, the mixture refluxed 2 h., decomposed with about 100 cc. cold saturated aqueous NH4Cl, and extracted with Et2O, the extract dried and evaporated, and the solid residue recrystallized from C6H6 and light petr. yielded about 0.73 g. 1-chloro-4-methylxanthydrol, colorless crystals, m. 170° (yellow melt). VI, XII, XIII, and XIV (1 g. each) in 25 cc. hot absolute EtOH added dropwise to 1 g. molten metallic Na by the method of Heller and Kostanecki (C.A. 2, 2243), the mixture steam distilled, and the resulting solid recrystallized from MeOH gave an almost quant. yield of I, m. 101°, in each case. III, IV, V (2 g. each) and 1.5 g. of the appropriate thiol in 25 cc. AmOH treated with 0.1 g. solid KOH, the mixture refluxed 3 h., held at room temperature overnight, and filtered, the filter residue washed with cold EtOH, H2O, and cold Me2CO, and extracted with about 60 cc. ligroine (b. 60-80°), and the residue crystallized from glacial AcOH gave the corresponding 1-arylmercapto-4-methylxanthones and -thiaxanthones. In this manner were obtained the following compounds (m.p. and % yield given): 1-(o-tolylmercapto)4-methylxanthones (XV), 170°, 52; the m-isomer, 163°, 58; the p-isomer of XV, 166°, 73; 1-phenylmercapto-6-chloro-4-methylxanthone (XVI), 164°, 81; the o-Me derivative of XVI, 205°, 62; m-Me derivative of XVI, 140°, 58; p-Me derivative of XVI, 180°, 78; 1-phenylmercapto-4-methylthiaxanthone (XVII), 150°, 83°; o-Me derivative of XVII, 162°, 64; m-Me derivative of XVII, 140°, 61; p-Me derivative of XVII, 164°, 84; all compounds formed yellow crystals and gave an orange-red color with H2SO4. The appropriate arylmercapto-4-methylxanthone or -thiaxanthone (1 g.) in 25 cc. glacial AcOH treated with 5 cc. 30% H2O2, the mixture heated 1 h. on the steam bath and held at room temperature overnight, and the resulting crystallized deposit recrystallized from glacial AcOH gave the corresponding sulfones (mercapto compound used, m.p., and % yield given): XV, 260°, 63; m-isomer of XV, 226°, 61; p-isomer of XV, 270°, 76; XVI, 210-12°, 84; o-Me derivative of XVI, 242°, 73; m-Me derivative of XVI, 198°, 69; p-Me derivative of XVI, 240°, 79; XVII, 176°, 82; o-Me derivative of XVII, 180°, 75; m-Me derivative of XVII, 182°, 70; p-Me derivative of XVIII, 210°, 85. I (1 g.) and 1.3 g. VI in 30 cc. C6H6 exposed 10 days (May) to sunlight and the resulting colorless needles washed with about 10 cc. C6H6 and recrystallized from hot C6H6 yielded about 80% VII, m. 174°; it dissolved with difficulty with an orange color in concentrated H2SO4. VIII (0.7 g.) and 0.5 g. I in 25 cc. C6H6 exposed 10 days (July) to sunlight, the C6H6 removed in vacuo, the oily residue cooled, and the semisolid mass washed with about 25 cc. petr. ether (b. 50-60°) and recrystallized from C6H6 yielded about 0.32 g. IX, m. 201°. The Grignard solution from 0.9 g. Mg and 9 g. PhBr in 50 cc. dry Et2O treated with 1 g. VI in 50 cc. dry C5H6, the Et2O evaporated, the residual mixture heated 1 h. on the steam bath, kept at 25° overnight, and poured slowly into 100 cc. saturated aqueous NH4Cl, the Et2O layer dried, filtered, and evaporated, the oily residue washed with about 35 cc. petr. ether below 40°, and the resulting solid crystallized from ligroine gave about 0.87 g. 2-chloro-9-phenylxanthydrol, m. 113°; it gave an orange color with H2SO4; it gave reduced with Zn dust and AcOH almost 100% X, colorless crystals, m. 139° (from EtOH). X (1 g.) in solution exposed 15 days (Apr.) to sunlight gave about 0.63 g. XI, m. 221° (decomposition) (brown-red melt); it gave an orange-yellow color with H2SO4. XI (0.5 g.) heated 0.5 h. at 270° yielded 0.18 g. xanthone. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Product Details of 100927-02-4).
4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 100927-02-4
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