Synthesis of p-toluenesulfonic acid

Preparation of p-toluenesulfonic acid

Preparation of p-toluenesulfonic acid

Preparation of p-toluenesulfonic acid

To 500 ml a round bottom flask, fitted with a dean stark, which is connected with reflux condenser, 100 ml of toluene and 20 ml of concentrated sulfuric acid (d = 1,84) are placed. The lower part of the dean stark trap additionally is filled with toluene.

A glass apparatus for the preparation of p-toluenesulfonic acid

A glass apparatus for the preparation of p-toluenesulfonic acid

The reaction flask is heated with reflux for 5-6 h at 160° C. When the reaction begins the droplets of water start to form. From time to time the water from the dean stark collector is lowered into a small measuring cylinder. After five hours of 12.5 ml of water is collected. The reaction continues until no more water is forming. When the reaction is complete heating is removed and reaction mixture is allowed to cool. After addition of few ml of water p-toluenesulfonic acid immediately crystallizes. The reaction product is filtered, washed with small amount of water. The purification is performed by dissolving in small amount of hot water and and treating with activated charcoal, then filtered into a conical flask and cooled with ice-salt. To this strongly cooled solution gaseous hydrogen chloride is passed leading to the formation of white crystals which are filtered and dried. p-toluenesulfonic acid crystallizes with one molecule of water and melts at 104-105 °C. Yield about 25 g.

Практические работы по органической химии, Ю.K.Юрьев, 138-139, 1964, (Practical work in organic chemistry, Yu.K.Yurev, 138-139, 1964)

IUPAC Name

4-methylbenzenesulfonic acid

InChI

InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)

InChI Key

JOXIMZWYDAKGHI-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

4-toluene sulfonate, 4-toluenesulfonic acid, 4-toluenesulfonic acid ammonium salt, 4-toluenesulfonic acid monohydrate, 4-toluenesulfonic acid, calcium salt, 4-toluenesulfonic acid, copper (2+) salt, 4-toluenesulfonic acid, ion (1+), 4-toluenesulfonic acid, lithium salt, 4-toluenesulfonic acid, magnesium salt, 4-toluenesulfonic acid, potassium salt, 4-toluenesulfonic acid, rubidium salt, 4-toluenesulfonic acid, silver (+1) salt, 4-toluenesulfonic acid, sodium salt, 4-toluenesulfonic acid, zinc salt, p-toluene sulfonate, p-toluene sulphonic acid, p-toluenesulfonate, p-toluenesulfonate pyridinium, p-toluenesulfonic acid, para-toluene sulfonate, para-toluenesulfonic acid

Depositor-Supplied Synonyms

P-TOLUENESULFONIC ACID, 4-Methylbenzenesulfonic acid, 104-15-4, 4-Toluenesulfonic acid, p-Toluenesulphonic acid, Tosic acid, p-Tolylsulfonic acid, Toluene-4-sulfonic acid, Benzenesulfonic acid, 4-methyl-, Eltesol, ar-Toluenesulfonic acid, p-Methylphenylsulfonic acid, PTSA, p-Methylbenzenesulfonic acid, Cyclophil P T S A, Tosylic acid, Benzenesulfonic acid, methyl-, p-Toluenesulfonate, p-Toluolenesulfonic acid, Methylbenzenesulfonic acid, PARA-TOLUENE SULFONATE, Manro PTSA 65 E, Manro PTSA 65 H, Nacure 1040, TSA-HP, TSA-MH, Manro PTSA 65 LS, P-Toluene Sulfonic acid, Cyzac 4040, p-Toluene sulfonate, Toluene-4-sulphonic acid, Kyselina p-toluenesulfonova, K-Cure 1040, Toluene-p-sulfonate, p-Toluene-sulfonic acid, 4-Toluene sulfonic acid, para-toluenesulfonic acid, Kyselina p-toluensulfonova, K-Cure 040, NSC 167068, Toluenesulfonic acid (VAN), UNII-QGV5ZG5741, CHEMBL541253, 4-TOLUENE-SULFONIC ACID, 4-methylbenzene-1-sulfonic acid, CHEBI:27849, HSDB 2026, JOXIMZWYDAKGHI-UHFFFAOYSA-N, Kyselina p-toluensulfonova [Czech], Kyselina p-toluenesulfonova [Czech], EINECS 203-180-0, BRN 0472690, AI3-26478, ST50825009, WLN: WSQR D1, TSU, tosyl alcohol, Cis-Tosylate, pTsOH, TsOH, p-toluenesulfonicacid, p-TsOH, p-toluensulfonic acid, 4-toluylsulfonic acid, p-toluene sulfonicacid, p-toluene-sulfonicacid, p-toluensulphonic acid, paratoluensulfonic acid, Toluen-4-sulfonsaeure, p-TSA, p-toluen sulfonic acid, p-toluenesuiphonic acid, p-toluenylsulfonic acid, toluene4-sulfonic acid, paratoluensulphonic acid, 2 -toluenesulphonicacid, 4-toluenesulphonic acid, p- toluenesulfonic acid, p-tolu-enesulfonic acid, p-toluyl sulphonic acid, PubChem16860, toluene-p-sulfonic acid, para-toluensulfonic acid, paratoluenesulphonic acid, p-toluene sulphonic acid, p-toluene-sulphonic acid, toluene 4-sulfonic acid, toluene p-sulphonic acid, toluene-p-sulphonic acid, para toluenesulfonic acid, paratoluene sulfonic acid, paratoluene-sulfonic acid, SCHEMBL34, 4-toluene sulphonic acid, 4-toluene-sulphonic acid, AC1Q2LRI, AC1Q2LRJ, para toluenesulphonic acid, para-toluenesulphonic acid, paratoluene sulphonic acid, para toluene sulfonic acid, para-toluene sulfonic acid, para-toluene-sulfonic acid, 4-methylbenzenesulfonicacid, DSSTox_CID_6701, 4-methylphenylsulfonic acid, para toluene sulphonic acid, para-toluene sulphonic acid, 4-methylphenylsulphonic acid, AC1L1LT3, ACMC-1C4C9, DSSTox_RID_78188, NCIOpen2_002932, NCIOpen2_003096, 4-methylbenzenesulphonic acid, DSSTox_GSID_26701, 4-methyl-benzenesulfonic acid, 4-methylbenzene sulfonic acid, 4-methylbenzene-sulfonic acid, KSC174O1N, 4-methyl benzene sulfonic acid, ar-Toluenesulfonic acid (8CI), QGV5ZG5741, 4-methyl-benzene-sulphonic acid, Jsp000415, Jsp003032, 6192-52-5 (monohydrate), CTK0H4716, NSC2167, 1470-83-3 (lithium salt), 4124-42-9 (ammonium salt), MolPort-001-783-159, 13438-45-4 (zinc salt), 657-84-1 (hydrochloride salt), 36747-44-1 (calcium salt), NSC-2167, 16106-44-8 (potassium salt), 51650-46-5 (magnesium salt), Tox21_202364, AC-794, ANW-15037, NSC167068, (2RS,3RS)-toluene-4-sulfonic acid, AKOS008966288, (2 RS,3RS)-toluene-4-sulfonic acid, AM90497, DB03120, MCULE-1176533515, NSC-167068, RP23449, RP23450, RTC-063995, 7144-37-8 (copper(2+) salt), (1RS,2RS,3SR)-p-toluenesulfonic acid, (1RS,2SR,3RS)-p-toluenesulfonic acid, NCGC00248146-01, NCGC00248146-02, NCGC00259913-01, 16836-95-6 (silver(+1) salt), AJ-26662, AK-53368, AN-15515, BC204518, CAS-104-15-4, KB-61760, TL806147, AB1002549, DB-050363, KB-204554, LS-154156, TC-063995, X8700, EN300-16830, 6720-EP1441224A2, 6720-EP2269610A2, 6720-EP2269977A2, 6720-EP2269989A1, 6720-EP2269990A1, 6720-EP2269994A1, 6720-EP2270011A1, 6720-EP2270012A1, 6720-EP2270013A1, 6720-EP2270114A1, 6720-EP2270505A1, 6720-EP2272537A2, 6720-EP2272822A1, 6720-EP2272832A1, 6720-EP2274983A1, 6720-EP2275404A1, 6720-EP2275411A2, 6720-EP2275418A1, 6720-EP2277848A1, 6720-EP2277858A1, 6720-EP2277861A1, 6720-EP2277866A1, 6720-EP2277867A2, 6720-EP2277878A1, 6720-EP2277880A1, 6720-EP2280000A1, 6720-EP2280003A2, 6720-EP2280009A1, 6720-EP2281817A1, 6720-EP2281818A1, 6720-EP2281820A2, 6720-EP2284148A1, 6720-EP2284159A1, 6720-EP2286812A1, 6720-EP2287147A2, 6720-EP2287152A2, 6720-EP2287155A1, 6720-EP2287160A1, 6720-EP2287166A2, 6720-EP2289518A1, 6720-EP2289868A1, 6720-EP2289876A1, 6720-EP2289883A1, 6720-EP2289887A2, 6720-EP2289888A2, 6720-EP2289893A1, 6720-EP2289965A1, 6720-EP2292231A1, 6720-EP2292234A1, 6720-EP2292576A2, 6720-EP2292592A1, 6720-EP2292610A1, 6720-EP2292611A1, 6720-EP2292620A2, 6720-EP2292621A1, 6720-EP2295055A2, 6720-EP2295401A2, 6720-EP2295402A2, 6720-EP2295406A1, 6720-EP2295409A1, 6720-EP2295414A1, 6720-EP2295416A2, 6720-EP2295423A1, 6720-EP2298729A1, 6720-EP2298731A1, 6720-EP2298735A1, 6720-EP2298743A1, 6720-EP2298747A1, 6720-EP2298748A2, 6720-EP2298754A1, 6720-EP2298755A1, 6720-EP2298763A1, 6720-EP2298767A1, 6720-EP2298770A1, 6720-EP2298772A1, 6720-EP2298778A1, 6720-EP2301536A1, 6720-EP2301538A1, 6720-EP2301544A1, 6720-EP2301909A1, 6720-EP2301918A1, 6720-EP2301922A1, 6720-EP2301933A1, 6720-EP2301934A1, 6720-EP2305219A1, 6720-EP2305257A1, 6720-EP2305627A1, 6720-EP2305633A1, 6720-EP2305641A1, 6720-EP2305647A1, 6720-EP2305649A1, 6720-EP2305650A1, 6720-EP2305651A1, 6720-EP2305655A2, 6720-EP2305662A1, 6720-EP2305672A1, 6720-EP2305677A1, 6720-EP2305681A1, 6720-EP2305682A1, 6720-EP2305685A1, 6720-EP2305686A1, 6720-EP2308562A2, 6720-EP2308838A1, 6720-EP2308839A1, 6720-EP2308840A1, 6720-EP2308841A2, 6720-EP2308849A1, 6720-EP2308850A1, 6720-EP2308851A1, 6720-EP2308854A1, 6720-EP2308857A1, 6720-EP2308869A1, 6720-EP2308871A1, 6720-EP2308874A1, 6720-EP2308877A1, 6720-EP2308879A1, 6720-EP2311453A1, 6720-EP2311455A1, 6720-EP2311804A2, 6720-EP2311808A1, 6720-EP2311809A1, 6720-EP2311810A1, 6720-EP2311811A1, 6720-EP2311814A1, 6720-EP2311815A1, 6720-EP2311827A1, 6720-EP2311829A1, 6720-EP2311838A1, 6720-EP2311841A1, 6720-EP2311842A2, 6720-EP2314574A1, 6720-EP2314575A1, 6720-EP2314577A1, 6720-EP2314584A1, 6720-EP2314585A1, 6720-EP2314586A1, 6720-EP2314587A1, 6720-EP2314588A1, 6720-EP2314593A1, 6720-EP2316457A1, 6720-EP2316458A1, 6720-EP2316825A1, 6720-EP2316826A1, 6720-EP2316827A1, 6720-EP2316828A1, 6720-EP2316831A1, 6720-EP2316836A1, 6720-EP2371811A2, 6720-EP2374790A1, 6720-EP2374895A1, C06677, 16415-EP2270008A1, 16415-EP2275401A1, 16415-EP2281563A1, 16415-EP2289890A1, 16415-EP2292617A1, 16415-EP2305646A1, 16415-EP2305657A2, 16415-EP2316459A1, 18563-EP2269992A1, 18563-EP2270002A1, 18563-EP2272848A1, 18563-EP2292615A1, 18563-EP2295433A2, 18563-EP2298742A1, 18563-EP2298746A1, 18563-EP2305660A1, 18563-EP2314576A1, 18563-EP2371805A1, 18812-EP2284160A1, 18812-EP2314576A1, 23307-EP2281820A2, 23307-EP2287159A1, 23307-EP2295420A1, 23307-EP2298754A1, 23307-EP2308867A2, 23307-EP2308870A2, 23307-EP2314584A1, 40089-EP2275410A1, 40089-EP2277866A1, 40089-EP2284169A1, 40089-EP2287161A1, 40089-EP2287162A1, 40089-EP2295410A1, 40089-EP2301920A1, 40089-EP2301939A1, 40089-EP2305647A1, 40089-EP2308861A1, 40089-EP2308867A2, 40089-EP2308870A2, 40089-EP2311804A2, 40089-EP2311830A1, 40089-EP2371814A1, 40089-EP2377849A2, 40089-EP2380874A2, 48861-EP2279741A2, 48861-EP2284174A1, 48861-EP2289509A2, 48861-EP2295437A1, 48861-EP2298775A1, 48861-EP2308867A2, 48861-EP2308870A2, 48861-EP2311841A1, 48861-EP2374787A1, 91583-EP2305668A1, 91583-EP2371814A1, 112898-EP2269988A2, 112898-EP2275413A1, 112898-EP2287156A1, 112898-EP2295437A1, 112898-EP2298775A1, 4-11-00-00241 (Beilstein Handbook Reference), 3B4-0158, I01-0454, InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10, 100901-72-2, 114213-96-6, 126033-27-0, 128739-80-0, 144647-92-7, 156627-46-2, 185568-48-3, 210357-81-6, 227313-49-7, 369371-25-5, 402-47-1, 51506-29-7, 613262-31-0, 70788-37-3

Removed Synonyms

Toluenesulfonic acid, tosylate, null, Toluene sulfonic acid, Toluene-4-sulfonate, Toluenesulphonic acid, CID6101, Aminomalononitrile p-toluenesulfonate, p-Toluenesulfonic acid, polymer-bound, H2380, T0267, 25231-46-3, 6192-52-5, 4846-75-7, 657-84-1

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