Methanol → Quadrol methacrylate

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(VI-a): Glycidyl methacrylate (5.0 g, 35.5 mmol) was added, dropwise, to a solution of N,N,N'-tris(2-hydroxypropyl)ethylenediamine (V-a) (8.3 g, 35.5 mmol) in 10 mL of CH2Cl2 at room temperature. 4-Methoxyphenol (0.03 g) was added to prevent polymerization. The reaction was maintained for 72 hours at room temperature, then warmed to 30° C. for an additional 24 hours. The reaction was followed by TLC (4 percent MeOH in CCl4 ; glycidyl methacrylate Rf 0.69). Quadrol methacrylate (VI-a) was obtained in quantitative yield after removal of the solvent. The product was further purified by dissolving 5 g of (VI-a) in 200 mL distilled water followed by addition of sodium chloride to saturation. The product, which separated out as an oil, was collected, dissolved in CH2Cl2, and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed to give Quadrol-methacrylate [yield, 53 percent; IR(neet):3350(broad OH); 1720(C=O); 1640(C=C); NMR(CDCl3 ): δ6.2(s, 1H); 5.6(s, 1H); 4.0(broad m, 6); 2.5(broad m, 12H); 2.0 (s, 3H); 1.1(d, 9H)].

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