Synthesis of benzyl p-toluenesulfonate

Preparation of benzyl p-toluenesulfonate

Preparation of benzyl p-toluenesulfonate

Preparation of benzyl 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. 10.9 ml of absolute benzyl alcohol 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 crystalline product was washed with heptane and water, and dried; yield, 10.5 g.; m.p. 55°C.

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

IUPAC Name

benzyl 4-methylbenzenesulfonate

InChI

InChI=1S/C14H14O3S/c1-12-7-9-14(10-8-12)18(15,16)17-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

InChI Key

OVHDZBAFUMEXCX-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=C(C=C1)S(=O)(=O)OCC2=CC=CC=C2

Depositor-Supplied Synonyms

Benzyl 4-toluenesulfonate, Benzyl tosylate, 1024-41-5, benzyl p-toluenesulfonate, Benzyl 4-methylbenzenesulfonate, CCRIS 5123, OVHDZBAFUMEXCX-UHFFFAOYSA-N, benzyltosylate, AC1L4NU6, AC1Q6Y6J, SCHEMBL2890, benzyl para-toluene sulfonate, CTK4A1102, DTXSID30145039, Benzyl 4-methylbenzenesulfonate #, ZINC2244243, AR-1H9488, AR-1H9489, MFCD01318299, ZINC02244243, Toluene-4-sulfonic acid, benzyl ester, OR061228, OR194747, 4-methyl-benzenesulfonic acid benzyl ester, KB-200525, LS-188224, B12000, Benzenesulfonic acid,4-methyl-, phenylmethyl ester

Removed Synonyms

CID160558, 11018-93-2, 11019-08-2

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