Synthesis of 4-toluenesulfonyl chloride

Preparation of 4-toluenesulfonyl chloride

Preparation of 4-toluenesulfonyl chloride

Preparation of 4-toluenesulfonyl chloride

130 g pure toluene are heated with 450 g concentrated sulfuric acid in a cast-iron pot fitted with a suitable agitator. A crystal of iodine is added, and the temperature allowed to rise to 100° C. The sulfonation is complete in about 6 hours, when the reaction mixture is transferred to a large basin, diluted with water, and limewater added gradually to neutralize the excess acid. The calcium sulfate and any ferric hydroxide present are removed by filtration and washed with hot water. Sodium carbonate is added to the filtrate until just alkaline to phenolphthalein, and the calcium carbonate is removed by filtration. The filtrate is then evaporated almost to dryness, when the sodium salts of 2-toluenesulfonyl and 4-toluenesulfonyl acids separate out. The total yield of 2-toluenesulfonyl and 4-toluenesulfonyl acids are 95% (340 g). o-sodium tosylate crystallizes with 2H2O as plates. p-Sodium tosylate crystallizes with 4H2O as plates or prisms. In order to obtain 2-toluenesulfonyl chloride and 4-toluenesulfonyl chloride the mixture prepared above is treated gradually with an equal weight of finely ground phosphorus pentachloride. When the reaction is complete, cold water is added, the reaction mixture being surrounded by a freezing mixture. The 4-toluenesulfonyl chloride separates as a solid (m.p. 69° C) purified by recrystallization from alcohol. The 2-toluenesulfonyl chloride is an oily liquid (m.p. 10° C), and is separated from the filtrate by means of a separatory  funnel.

Systematic organic chemistry, by W. M. Cumming, 312, 1937.

IUPAC Name

4-methylbenzenesulfonyl chloride

InChI

InChI=1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3

InChI Key

YYROPELSRYBVMQ-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=C(C=C1)S(=O)(=O)Cl

MeSH Synonyms

4-toluenesulfonyl chloride, p-toluenesulfonyl chloride, tosyl chloride

Depositor-Supplied Synonyms

Tosyl chloride, P-TOLUENESULFONYL CHLORIDE, 98-59-9, 4-Methylbenzenesulfonyl chloride, p-Tosyl chloride, 4-Toluenesulfonyl chloride, 4-methylbenzene-1-sulfonyl chloride, p-Tolylsulfonyl chloride, Benzenesulfonyl chloride, 4-methyl-, p-Toluenesulphonyl chloride, p-Toluenesulfochloride, p-Methylbenzenesulfonyl chloride, para-Toluenesulfonyl chloride, tosylchloride, p-Toluenesulfonic acid chloride, 4-toluene sulfonyl chloride, p-toluenesulfonylchloride, para-Toluenesulfochloride, p-toluensulfonyl chloride, p-Toluenesulfonic chloride, toluene-4-sulfonylchloride, p-toluene sulfonyl chloride, NSC 175822, p-Toluene sulphonyl chloride, Toluene-4-sulfonyl chloride, 4-methylbenzenesulfonylchloride, p-Methylphenylsulfonyl chloride, UNII-027KYN78B4, 4-methylphenylsulfonyl chloride, Toluenesulfonyl chloride (VAN), 4-Toluenesulfonic acid, chloride, HSDB 5317, 4-methyl-benzenesulfonyl chloride, YYROPELSRYBVMQ-UHFFFAOYSA-N, EINECS 202-684-8, SBB040936, AI3-52254, 4-Methyl-benzenesulfonylchloride, tosyl-chloride, TsCl, 4-Tosyl chloride, p-TsCe, p-Toluensulfonylchloride, PubChem10215, ACMC-209sap, p-toluensulphonylchloride, 4-toluenesulfonylchloride, 4toluenesulfonyl chloride, p-toluenesulphonylchloride, 4-toluensulfonyl chloride, 4-toluylsulfonyl chloride, AC1Q2LRG, AC1Q6YLS, p-tolyl-sulfonyl chloride, 4-toluenesulphonylchloride, p-toluene sulfonylchloride, p-toluene-sulfonylchloride, p-toluenesulfonyl-chloride, p-toluensulphonyl chloride, p-toluene sulphonylchloride, p-toluenesulfonoyl chloride, para-tolylsulfonyl chloride, toluene-p-sulphonylchloride, para-toluenesulfonylchloride, 4-toluene-sulphonylchloride, 4-toluenesulphonic chloride, 4-toluenesulphonyl chloride, p -toluenesulfonyl chloride, p- toluenesulfonyl chloride, p-toluen-sulphonyl chloride, p-toluene sulfonic chloride, p-toluene-sulfonyl chloride, toluene-p-sulfonyl chloride, toluene4-sulphonyl chloride, para-toluensulfonyl chloride, Toluene p-sulfonyl chloride, Toluene-4-sulphonylchloride, 4-toluene-sulfonyl chloride, AC1L1OO4, p-toluene-sulphonyl chloride, paratoluenesulphonyl chloride, SCHEMBL1586, toluene p-sulphonyl chloride, toluene-p-sulphonyl chloride, para toluenesulfonyl chloride, para-toluene sulfonylchloride, paratoluene sulfonyl chloride, toluene-4-sulphonyl chloride, 4-Toluene-sulphonyl chloride, chloro(4-methylphenyl)sulfone, p-toluene- sulphonyl chloride, para-toluenesulphonyl chloride, T35955_ALDRICH, KSC486M3P, para-toluene sulfonyl chloride, para-toluene-sulphonyl chloride, Para toluene sulphonyl chloride, Para-toluene sulphonyl chloride, 240877_ALDRICH, 4-methyl-phenylsulphonylchloride, 4-methylphenylsulphonyl chloride, 4-methylbenzenesulphonyl chloride, 4-methylbenzenesulphonyl-chloride, p-methyl benzenesulfonyl chloride, 4-methyl benzenesulfonyl chloride, 4-methylbenzene sulfonyl chloride, 4-methylphenyl-sulphonyl chloride, 89730_FLUKA, CTK3I6637, T35955_SIAL, (4-methylphenyl)sulfonyl chloride, 4-methyl-benzenesulphonyl chloride, 4-methylbenzene sulphonyl chloride, MolPort-000-872-098, p-Toluenesulfonyl chloride (8CI), 027KYN78B4, 4-methyl benzene sulfonyl chloride, 4-methylbenzene-1-sulfonylchloride, Benzenesulfonylchloride, 4-methyl-, 240877_SIAL, ANW-40943, AR-1L2568, BR1703, NSC175822, STK298722, ZINC59699249, AKOS000120295, MCULE-5162213626, NSC-175822, RP25022, RTR-038634, AK-51783, AM101769, AN-24487, BC650741, BP-20587, BR-51783, KB-39911, OR025210, OR382359, SC-07509, AB0007849, AB1002186, KB-195416, LS-185773, ST2411537, TR-038634, FT-0619534, T-3900, Z-1442, 10064-EP2281818A1, 10064-EP2287167A1, 10064-EP2292576A2, 10064-EP2292610A1, 10064-EP2292621A1, 10064-EP2292628A2, 10064-EP2295416A2, 10064-EP2295441A2, 10064-EP2298734A2, 10064-EP2298735A1, 10064-EP2298748A2, 10064-EP2298768A1, 10064-EP2305682A1, 10064-EP2305808A1, 10064-EP2308510A1, 10064-EP2308869A1, 10064-EP2308879A1, 10064-EP2311824A1, 10064-EP2311837A1, 10064-EP2316835A1, 10064-EP2371811A2, 11183-EP2269977A2, 11183-EP2270015A1, 11183-EP2270114A1, 11183-EP2275407A1, 11183-EP2275411A2, 11183-EP2277880A1, 11183-EP2280000A1, 11183-EP2284159A1, 11183-EP2284169A1, 11183-EP2284174A1, 11183-EP2287161A1, 11183-EP2287162A1, 11183-EP2289887A2, 11183-EP2289888A2, 11183-EP2289893A1, 11183-EP2292610A1, 11183-EP2292628A2, 11183-EP2295406A1, 11183-EP2295441A2, 11183-EP2298747A1, 11183-EP2298768A1, 11183-EP2298778A1, 11183-EP2301536A1, 11183-EP2301538A1, 11183-EP2305633A1, 11183-EP2305646A1, 11183-EP2305668A1, 11183-EP2305684A1, 11183-EP2308812A2, 11183-EP2308851A1, 11183-EP2308869A1, 11183-EP2308877A1, 11183-EP2311455A1, 11183-EP2311801A1, 11183-EP2311802A1, 11183-EP2311803A1, 11183-EP2311822A1, 11183-EP2311824A1, 11183-EP2311837A1, 11183-EP2316457A1, 11183-EP2316827A1, 11183-EP2371814A1, 11183-EP2371831A1, 37335-EP2311802A1, 37335-EP2311803A1, 37370-EP2311802A1, 37370-EP2311803A1, 38724-EP2308873A1, 38724-EP2311837A1, 66306-EP2272827A1, 66306-EP2308851A1, 72304-EP2308867A2, 72304-EP2308870A2, 72304-EP2308877A1, 112910-EP2295437A1, 112910-EP2298775A1, I01-4508, W-110674, 3B3-030179, InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H, methyl (2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-guanidino-pentanoate

Removed Synonyms

Toluenesulfonyl chloride, Toluenesulphonyl chloride, CID7397, T0272, 6272-09-9

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