Huntress, Ernest H. published the artcileIdentification of organic compounds. IV. Chlorosulfonic acid as a reagent for identification of alkylbenzenes, Recommanded Product: 5,6,7,8-Tetrahydronaphthalene-2-sulfonyl chloride, the publication is Journal of the American Chemical Society (1941), 3446-8, database is CAplus.
cf. C. A. 34, 2804.4. The use of ClSO3H has been extended to 37 aromatic hydrocarbons. The process of part I (C. A. 34, 2803.9) was used except that 5 mL. of ClSO3H was used and the reaction product was stirred 45 min. before pouring it onto ice; the chloride was converted by solid (NH4)2CO3 to the amide. The structures of the amides of the monoalkylated benzenes were established by KMnO4 oxidation of the side chain and indicated that the chlorosulfonylation occurred in the p-position to the side chain. For the polyalkylated benzenes the structures were inferred from previous work. The derivative of C6H6, the derivative of the benzenesulfonamide, the m. p. and yield are given. C6H6, PhSO2NH2, 150-50.5° 23%; Me, 4-Me, 135.5-6°, 36-44%; Et, 4-Et, 109-10° 73-95%; 1,2-Me2, 3,4-Me2, 143-4°, 67%; 1,3-Me2, 2,4-Me2, 136.5-7° 78%; 1,4-Me3, 2,5-Me2, 145.5-6°, 84%; Pr, 4-Pr, 107-8°, 65-95%; iso-Pr, 4-iso-Pr, 104.5-5.5°, 82-8%; 1,2,4-Me3, 2,4,5-Me3, 175-6°, 52%; 1,3,5-Me3, 2,4,6-Me3, 141.5-2.5°, 57%; Bu, 4-Bu, 94.5-5°, 80%; sec-Bu, 4-sec-Bu, 81-2.5°, 63-72%; tert-Bu, 4-tert-Bu, 136-7°, 100%; iso-Bu, 4-iso-Bu, 84-5°, 82%; 1,4-Me(iso-Pr), 2,5-Me(iso-Pr), 114.5-15.5°, 84-7%; 1,3-Et2, 2,4-Et2(?), 98-9°, 57-8%; 1,3,4-Me2Et, 2,4,5-Me2Et(?), 147-8°, 80-5%; 1,2,3,4-Me4, 2,3,4,5-Me4, 183.5-4°, 85%; 1,2,3,5-Me4, 2,3,4,6-Me4, 141.5-2°, 82%; 1,2,4,5-Me4, 2,3,5,6-Me4, 153-4°, Am, 4-Am, 85.5-6.5°, 80-100%; tert-Am, 4-tert-Am, 83-4°, 89-90%; 1,3,4-Me2Pr, 2,4,5-Me2Pr(?), 90-3°, 79-82%; 1,3,4-Me2(iso-Pr), 2,4,5-Me2(iso-Pr)(?), 155.5-6°, 68%; 1,3,5,2-Me3Et, 2,4,6,3-Me3Et, 131-2°, 64-71%; Me5, Me5, 182-3° 90-2%; hexyl, 4-hexyl, 85-5.5°, 81%; 1,3,4-Me2(tert-Bu), gives an amide m. 128-30° (81%); 1,3,5-Me2(tert-Bu), 2,4,6-Me2(tert-Bu)(?), 132-3°, 86%; 1,3,5-Et3, 2,4,6-Et3, 118-18.5°, 94%; 1,4-di-tert-Bu, 2,5-di-tert-Bu, 135.5-6.5°, -; nonyl, 4-nonyl, 94.5-5° 54-67%; hendecyl, 4-hendecyl, 95.7-6.2°, ; cyclohexyl, 4-cyclohexyl, 160-60.5°, 85-7%; 1,2,4,5-tetra(iso-Pr), 2,3,5,6-tetra-iso-Pr, 154.5-5° 60-85%. The following 1-benzenesulfonyl chlorides were isolated: 4-Me, 64-6°, 61-5%; 3,4-Me2, 52°, 74-86%; 2,4,6-Me3, 50-3°, 65-72%; 4-tert-Bu, 80-2°, 100%; 2,3,4,5-Me4, 72-3°, 95%; 2,3,5,6-Me4, 98-9°, 100%; Me5 77-8.5°, 98%; 2,4,6-Me2(tert-Bu), 65-7°, 97%; 4-cyclohexyl, 51-2.5°; 2,3,5,6-tetra(iso-Pr), 141.5-42°, 77-86%. The amount of sulfone formation was considerable (27%) only in the case of C6H6; PhMe gives 1-10%, PhEt 1-6%, iso-PrPh 2-3%, but the other hydrocarbons gave no evidence of corresponding products. Hydrindene gives 65-70% of the 5-sulfonamide, m. 132.5-3.5°; 1,2,3,4-tetrahydronaphthalene gives 75% of 5,6,7,8-tetrahydro-2-naphthalenesulfonamide, m. 134.5-5°; the sulfonyl chloride m. 58-8.5°.
Journal of the American 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, Recommanded Product: 5,6,7,8-Tetrahydronaphthalene-2-sulfonyl chloride.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
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