Synthesis
In a 250 mL round bottom flask, 2-methoxyethanol (7.36 mL, 0.10 mol) and a catalytic amount of tetra-n-butylammonium bromide (TBAB) were dissolved in methylene chloride (50 mL) and mixed with stirring. Subsequently, 30% aqueous sodium hydroxide solution (15 mL) was slowly added. A dichloromethane solution of p-toluenesulfonyl chloride (20 mL) was added dropwise under cooling in an ice water bath. After the dropwise addition was completed, the ice water bath was removed and the reaction mixture was stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was washed with distilled water (3 × 30 mL) to remove water-soluble impurities. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator under reduced pressure to give the yellow oily product 2-methoxyethyl p-toluenesulfonate in 95% yield. The product was confirmed by infrared spectroscopy (KBr press), and the main absorption peaks were: 3468 (m), 2938 (s), 2889 (s), 1597 (m), 1455 (m), 1357 (s), 1184 (s), 1130 (m), 1101 (m), 1018 (m), 919 (m), and 821 (m) cm^-1. The NMR hydrogen spectrum ( 400 MHz, acetone-d6) data are as follows: δ 3.20 (s, 3H), 3.48 (t, J = 4.6 Hz, 2H), 4.08 (t, J = 4.6 Hz, 2H), 7.71 (d, J = 8.4 Hz, 2H), 7.28 (d, J = 8.4 Hz, 2H), 2.36 (s, 3H). Elemental analysis results: calculated values for C10H14SO4: C, 52.16; H, 6.13. measured values: C, 52.09; H, 6.17.
References
[1] Dalton Transactions, 2007, # 13, p. 1309 - 1315
[2] Journal of Organometallic Chemistry, 2011, vol. 696, # 8, p. 1687 - 1690
[3] Chemistry of Materials, 2012, vol. 24, # 9, p. 1583 - 1590
[4] Dyes and Pigments, 2013, vol. 97, # 2, p. 278 - 285
[5] New Journal of Chemistry, 2016, vol. 40, # 4, p. 3456 - 3463
