Davies, W. published the artcilePolymerization of thiophene derivatives. V. The self-condensation of 4,5- and 6,7-benzothianaphthene 1,1-dioxides. A new route to 1-(1-naphthyl)- and 4-(2-naphthyl)phenanthrene, Related Products of chlorides-buliding-blocks, the publication is Journal of the Chemical Society (1956), 2609-14, database is CAplus.
cf. C.A. 50, 1752d. 2-(1-Naphthyl)ethanol, b0.2 130-2°, with PBr3 gave 2-(1-naphthylethyl) bromide (I). I (98 g.) was refluxed and stirred 15 hrs. with 170 g. of Na2SO3.7H2O to give 81 g. of Na 2-(1-naphthyl)ethanesulfonate (II). II stirred 30 min. with 66 g. PCl5 at room temperature, the mixture warmed 30 min. on a steam bath and extracted with Et2O, and the extract cooled precipitated gave 48 g. 2-(1-naphthyl)ethanesulfonyl chloride (III), m. 48-8.5°; anilide, m. 133.5-34°; amide, m. 172.5-73°. III (40 g.) in 75 ml. PhNO2 was added to 24 g. powd. AlCl3 in 200 ml. PhNO2, the mixture kept 1 hr. at room temperature and 2 hrs. at 70°, the complex decomposed with dilute HCl, the solvent steam distilled, and the residue extracted with C6H6 gave 14.8 g. 2,3-dihydro-4,5-benzothianaphthene 1,1-dioxide (IV), m. 178-8.5°. IV (6.0 g.) refluxed 8 hrs. with 4.8 g. N-bromosuccinimide and 0.1 g. Bz2O2 in 150 ml. CCl4, the solvent removed, and the residue dissolved in hot C6H6, filtered, and chromatographed on Al2O3 gave 2.7 g. 4,5-benzothianaphthene 1,1-dioxide (V), m. 136-7° or 141-2° with evolution of SO2. V was reduced with LiAlH4 to give 2,3-dihydrothianaphthene (VI), m. 86.5-87°. VI refluxed with chloranil in xylene 6 hrs. and the mixture cooled, filtered, diluted with C6H6, and chromatographed gave 4,5-benzothianaphthene. V (2.5 g.) in 50 ml. xylene was refluxed until evolution of SO2 ceased. Evaporation gave 1.6 g. 10,11-dihydro-9-thia-5,6-benzonaphtho(1′,2′,3,4)fluorene 9,9-dioxide (VII), m. 226°. VII refluxed 10 min. in 50% aqueous KOH in (HOCH2CH2)2O and the mixture diluted with H2O and extracted with Et2O gave 1-(1-naphthyl)phenanthrene, m. and mixed m.p. 115-16°. By the same sequence of reactions, the following compounds were prepared from 2-(2-naphthyl)ethanol, m. 66°: Na 2-(2-naphthyl)ethanesulfonate; 2,2′-naphthylethanesulfonyl chloride, m. 66-6.5° (amide, m. 200-200.5°); 2,3-dihydro-6,7-benzothianaphthene 1,1-dioxide, m. 187.5-88°; 6,7-benzothianaphthene 1,1-dioxide, m. 181-2°or 194-5° (decomposition); 10,11-dihydro-9-thia-7,8-benzonaphtho(2′,1′-3,4)fluorene 9,9-dioxide, m. 166-7°; and 4-(2-naphthyl)phenanthrene, m. 105-6°. 6-Tetralinsulfonyl chloride, m. 57-8°, was reduced with Zn and H2SO4 to 6-mercaptotetralin (VIII), b35 161-2°. VIII added to still-reacting Na in EtOH, followed by chloroacetal and NaBr, the mixture refluxed 6 hrs., the solution extracted with 2% aqueous NaOH, then Et2O, the Et2O extract distilled gave (6-tetralylthio)acetaldehyde di-Et acetal (IX), b0.5 160-1°. Slow addition of IX to mixed P2O5 and H3PO4 gave a yellow oil which was distilled to give a mixture of tetrahydrobenzothianaphthenes, b0.3 119-21°. Tetralin (50 g.) stirred 1 hr. into ClSO3H at -5° warmed to room temperature, the mixture precipitated with ice and extraction with CCl4, and the extract evaporated gave a mixture of 68 g. of 5- and 6-tetralinsulfonyl chlorides; this product (20 g.) added to 14.5 g. ClCH2CO2H on 12 g. NaOH in 250 ml. H2O and the mixture heated 1 hr. on a water bath, cooled, and acidified precipitated 25 g. of an acid mixture (X). X (20 g.) in 80 ml. 5% KOH was added to 40 ml. 40% KOH. The acidified precipitate gave 9.2 g. (6-tetralylthio)acetic acid, m. 78.5-79. Acidification of the filtrate gave 9.0 g. of (5-tetralylthio)acetic acid, m. 133-4°.
Journal of the Chemical Society published new progress about 61551-49-3. 61551-49-3 belongs to chlorides-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 5,6,7,8-Tetrahydronaphthalene-2-sulfonyl chloride, and the molecular formula is C10H11ClO2S, Related Products of chlorides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
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