ChemicalBook CAS DataBase List BENZENESULFONIC ACID PHENYL ESTER

BENZENESULFONIC ACID PHENYL ESTER synthesis

6synthesis methods

Product Name:BENZENESULFONIC ACID PHENYL ESTER
CAS Number:4358-63-8
Molecular formula:C12H10O3S
Molecular Weight:234.27

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108-95-2 Synthesis

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Yield:4358-63-8 97%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 6 h;Inert atmosphere;

Steps:

General procedure for the preparation of aryl benzenesulfonates

To a stirred solution of phenol (1a) (5.00 g, 53.1 mmol) in CH₂Cl₂ (100 mL) at 0 °C, benzenesulfonyl chloride (8.21 mL, 63.8 mmol) and Et₃N (8.83 mL, 63.8 mmol) were added. The reaction mixture was warmed to room temperature and stirred for 6 h. The mixture was quenched with 1 M HCl solution, extracted with CH₂Cl₂, dried over Na₂SO₄, and concentrated under reduced pressure. The crude product was purified by SiO₂ flash column chromatography (hexane:EtOAc 9:1 3:1) to give phenyl benzenesulfonate 2a (12.1 g, 51.7 mmol) in 97% yield as colorless viscous liquid. Data^[20]: ¹H NMR (CDCl₃, 400 MHz) δ 7.82 (d, J 7.2 Hz, 2H), 7.66 (t, J 6.4 Hz, 1H), 7.51 (t, J 7.6 Hz, 2H), 7.30-7.22 (m, 3H), 6.96 (d, J 7.6 Hz, 2H) ppm.