Synthesis of ethyl p-toluenesulfonate

Preparation of ethyl p-toluenesulfonate

Preparation of ethyl p-toluenesulfonate

Preparation of ethyl p-toluenesulfonate

22g of tosyl chloride were dissolved in 88 ml of dry pyridine (the temperature rising from 22°C to 24°C), and the solution was cooled to -10°C. 6.1 ml of absolute ethanol  were added, the temperature rising to -5°C after 2 minutes and then falling to – 10°C. Crystallization commenced after a further 3 minutes, and the mixture was kept at -10°C for 15 minutes more. Sulfuric acid (280 ml of 5N, cooled to 0°C) was added rapidly, with cooling. The temperature rose to 27°C, the crystals dissolved and the solution became opalescent. On cooling to +4°C, material crystallized out. It was filtered off, thoroughly washed with water, and dried; yield, 15 g.; m.p. 32°C.

J. Org. Chem., 1944, 09 (3), pp 235–241

IUPAC Name

ethyl 4-methylbenzenesulfonate

InChI

InChI=1S/C9H12O3S/c1-3-12-13(10,11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3

InChI Key

VRZVPALEJCLXPR-UHFFFAOYSA-N

Canonical SMILES

CCOS(=O)(=O)C1=CC=C(C=C1)C

Depositor-Supplied Synonyms

Ethyl p-toluenesulfonate, 80-40-0, Ethyl tosylate, Ethyl 4-methylbenzenesulfonate, Ethyl p-tosylate, Ethyl p-TS, p-Toluenesulfonic acid, ethyl ester, ETHYL P-METHYLBENZENESULFONATE, Benzenesulfonic acid, 4-methyl-, ethyl ester, Ethyl-p-toluenesulfonate, ethyl p-toluene sulfonate, Ethyl PTS, p-Toluolsulfonsaeure aethyl ester, NSC 8887, Ethyl toluene-4-sulfonate, Ethyl toluene-4-sulphonate, UNII-2160N0YURF, Ethyl p-methyl benzenesulfonate, CCRIS 1028, HSDB 5235, VRZVPALEJCLXPR-UHFFFAOYSA-N, p-Toluenesulfonic Acid Ethyl Ester, EINECS 201-276-7, Ethylester kyseliny p-toluensulfonove, SBB060597, BRN 0611213, AI3-08004, p-Toluolsulfonsaeure aethyl ester [German], Ethylester kyseliny p-toluensulfonove [Czech], Mittel AEP, ethyl p-toluensulfonate, PubChem17403, ACMC-209pje, Ethyl 4-toluenesulfonate, ethyl-p-toluene-sulfonate, ethyl-p-toluene sulphonate, Ethyl para-toluenesulfonate, AC1L1MZ1, AC1Q6Y5V, p-toluenesulfonic acid ethyl, ethyl4-methylbenzenesulfonate, WLN: 2OSWR D1, SCHEMBL76249, ethyl-P-methylbenzenesulfonate, KSC489Q6R, 104256_ALDRICH, 2160N0YURF, DTXSID2058833, 89770_FLUKA, CTK3I9868, Ethyl 4-methylbenzenesulfonate #, NSC8887, ethyl 4-methyl-1-benzenesulfonate, ethyl 4-methylbenzene-1-sulfonate, NSC-8887, toluene-4-sulfonic acid ethyl ester, ZINC1648308, ANW-37368, AR-1I9276, MFCD00009100, STL268850, ZINC01648308, Ethyl ester of p-Toluenesulfonic acid, AKOS000120217, MCULE-1801575459, NE10632, TRA0083208, 4-Methylbenzenesulfonic acid ethyl ester, 4-methyl-benzenesulfonic acid ethyl ester, AK198644, AN-24021, CJ-05944, CJ-26666, KB-51650, OR034007, SC-77152, DB-031914, LS-154168, TR-033453, FT-0626235, ST50825449, T0268, Y2044, 4-11-00-00248 (Beilstein Handbook Reference), I01-6341, F0001-2084, InChI=1/C9H12O3S/c1-3-12-13(10,11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H, 1195611-43-8

Removed Synonyms

ethyl paratoluene sulphonate, C9H12O3S, Benzenesulfonic acid, ethyl ester, CID6638, MolPort-001-768-950, RTR-033453, 84771-76-6

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