2-Methoxyethyl p-toluenesulfonate

A solution of 2-methoxyethanol (7.36 mL, 0.10 mol) and a catalytic amount of TBAB (tetra-n-butylammonium bromide) in dichloromethane was stirred, and subsequently NaOH (aq., 30percent, 15 mL) was added. A solution of p-toluenesulfonyl chloride in dichloromethane was added dropwise. The mixturewas stirred for 24 h at room temperature, and then washed with distilled water three times. The product was dried over Na2SO4, the solvent was removed under reduced pressure to give a yellow oil. Yield 95percent. IR (KBr, cm 1) selected bands: 3468 (m), 2938 (s), 2889 (s), 1597 (m), 1455 (m), 1357 (s), 1184 (s), 1130 (m), 1101 (m), 1018 (m), 919 (m), 821 (m). 1H-NMR (400 MHz, CD3COCD3): 3.20 (s, 3H), 3.48 (t, J ¼ 4.6 Hz, 2H), 4.08 (t, J ¼ 4.6 Hz, 2H), 7.71 (d, J ¼ 8.4 Hz, 2H), 7.28 (d, J ¼ 8.4 Hz, 2H), 2.36 (s, 3H). Anal. Calc. for C10H14SO4: C, 52.16; H, 6.13. Found: C, 52.09; H, 6.17.Synthesis of IronfflD chloride mgso-tetrakis-2-(N-(2-methoxy)ethγQpyridyl porphyrin; Synthesis of 2-methoxyethyl tosylate; 2-methoxyethanol (0.989 g, 13 mmol) was dissolved in 30 ml dichloromethane, and triethylamine (2.53 g, 25 mmol) was added to the solution. The reaction mixture was set to stir in an ice-water bath, and p-toluenesulfonyl chloride (3.22 g, 17 mmol) was added all at once. The ice was allowed to melt, and the reaction was continued overnight. The reaction mixture was then filtered, to remove all of the triethylamine hydrochloride, and the filtrate was washed with 30 ml saturated NaHCCfyaq), then 30 ml IN KHSψ4(General procedure: Three separate flasks were prepared; flask 1 was composed of p-toluenesulfonylchloride (TsCl) (237.0 mmol) dissolved in THF (74 mL), flask 2 had NaOH (367.0 mmol) dissolved in H2O (74 mL), flask 3 was composed of the alcohol (131.0 mmol) dissolved in THF (74 mL). Flask 2 and 3 were combined and then to an addition funnel flask 3 was added to it and placed over the flask 2 and 3 mixture to be added dropwise for 12h at room temperature, tracked by TLC. The reaction was quenched with water (100 mL) and extracted with DCM (2 x 60 mL) dried over anhydrous Na2S0To 150 mL of THF cooled to 0°C was added NaOH (15.8 g in 75 mL H2O), followed byaddition of 2-methoxyethanol (20.0 g, 260 mmol). p-Toluenesulfonyl chloride (50.11 g, 260mmol) was added in 3 portions over 30 min. The reaction was allowed to stir at roomtemperature overnight. The reaction was quenched by the addition of 200 mL H2O. The layerswere allowed to separate and the aqueous layer was extracted twice with CHTo a stirred solution of 2-methoxyethan-1-ol (2.0 g, 26.28 mmol, 1.0 eq) in DCM (30mL) at 0 oc was added TEA (14.6 mL, 105.12 mmol, 4.0 eq) followed by paratoluenesulfonylchloride (5.99 g, 31.53 mmol, 1.2 eq). The reaction mixture was changed toroom temperature and stirred for overnight. After completion of the reaction (monitored byTLC), the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate25 (2x100 mL). The combined organic layers were washed with water (50 mL) and brinesolution (20 mL). The organic layer was dried over Na2S04, filtered and evaporated underreduced pressure. The residue was purified by silica gel column chromatography by using40percent ethyl acetate in hexane as an eluent to obtain the title compound ( 4.3 g, yield: 71.6percent) asa liquid. 1H NMR (300 MHz, CDCb): 8 ppm 7.80 (d, J = 8.4 Hz, 2H), 7.35 (d, J = 8.1 Hz, 30 2H), 4.15 (t, J = 4.8 Hz, 2H), 3.57 (t, J = 4.8 Hz, 2H), 3.30 (s, 3H), 2.44 (s, 3H); ESI-MS:m/z 252.96 (M+Na)+To a stirred solution of 2-methoxyethanol (10 g, 131.4mmol, 1.0 eq) in CHTo a solution of 2-methoxyethanol (12-1, 5.00 g, 65.7 mmol) in CH

Molecular Weight:230.28
XLogP3:1.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:230.06128010
Monoisotopic Mass:230.06128010
Topological Polar Surface Area:61
Heavy Atom Count:15
Complexity:260
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes