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One hundred milliliters of 30% aqueous hydrogen peroxide (CAUTION) was extracted with diethyl ether (8 x 30 mL). The combined ethereal extracts were dried over MgSO4 for 3 hrs. Assay of the solution by iodometric titration was found to be ca. 2 M.
To a stirred solution of AcOH (1 mL) and the ethereal solution of H2O2 (210 mL, 0.515 mole) was added MgSO4 (25 g) and followed by the addition of ?-chloromethyl methyl sulfide (10 g, 0.104 mole) in diethyl ether (10 mL) at such rate that the solution was maintained at gentle reflux. After addition was completed, the mixture was refluxed for 10 h and then stirred for additional 20 h. The solid was filtered off and washed with diethyl ether (100 mL). To the organic solution was added water (5 mL) and slowly Na2SO3 (10 g) in order to destroy peroxides and excess hydrogen peroxide, then the mixture was stirred overnight. The ethereal layer was separated and the solvent evaporated to give white crystals which were triturated with hexane-diethyl ether (5:1) and recrystallized from EtOH to give 11.9 g (89%) of white needles, mp. 56—57°C, lit. 57—58°C.
1H NMR (200 MHz, CDCl3): δ 4.66 (s, 2H), 3.06 (s, 3H).
Anal. Calcd for C2H5ClSO2: C, 18.68; H, 3.92; Cl, 27.57. Found: C, 18.41; H, 4.18; Cl, 27.85
© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru