Search in database (English)
A solution of undistilled [(2-chloroethyl)thio]benzene (17.3 g, 100 mmol) and acetic acid (100 mL) was stirred by magnet bar in a 250-mL, two-neck flask and heated to 48 °C. A solution of hydrogen peroxide (31.7 g, 280 mmol, 27.5% aqueous solution) in acetic acid (50 mL) was added dropwise during 40 min at 40—49 °C, with cooling with a water bath as needed. The cloudy solution was heated to 70 °C and kept at 70 °C by a constant temperature oil bath for 4 h. The bath temperature was raised to 90 °C and held for 11 h. The white, cloudy mixture was cooled and water (200 mL) added to give a suspension of [(2-chloroethyl)sulfonyl]benzene. Diethyl ether (180 mL, and 40 mL) was added to extract the product and the ether layer washed in turn with brine and with water (50 mL, each) and dried (MgSO4). The salt cake was extracted with ether and the solvent stripped by rotary evaporator (50 °C/13 mm, 2 h) to give [(2-chloroethyl)sulfonyl]benzene, 17.8 g. The solid melted incompletely and thus contained salt. The sulfone was washed with water by suspension and collected on a filter, dried at 25 °C, dissolved in warm benzene (75 mL), filtered, and evaporated to dryness (rotary evaporator), 16.10 g; mp 55—57.5 °C (lit. mp 55 °C, 78.5% yield). Additional [(2-chloroethyl)sulfonyl]benzene (1.73 g, mp 55—57 °C) was recovered by evaporating the aqueous extracts and the salt cake in a beaker followed by trituration with water (200 mL) and fitration. The total yield of [(2-chloroethyl)sulfonyl]benzene was 87.1%. In view of the difficulty in extraction by diethyl ether of pure product, it would have been preferable to filter the original aqueous suspension of [(2-chloroethyl)sulfonyl]benzene and remove salt by water washing.
© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru