[Synthesis]
The general procedure for the synthesis of 5-chloro-1-pentanol from 5-chloropentyl acetate was as follows: 5-chloropentanol-1-acetate (33.9 g, 0.21 mol) was mixed with 95% ethanol (75 mL) and 2N aqueous NaOH (90 mL) according to the method reported by Meyers et al. (Tetrahedron 27, 5979-85), and shaken to homogeneous. The mixed solution was allowed to stand at room temperature for a few hours and the ethanol was subsequently removed by distillation under reduced pressure. The residue was extracted with ether (3 x 150 mL). The extract was dried over anhydrous potassium carbonate, the solvent was removed under reduced pressure and finally 5-chloro-1-pentanol was obtained by distillation as a colorless oil (21.1 g, 84% yield, literature value 72%) with a boiling point of 35-37°C (0.02 mmHg) (literature value 62°C (0.5 mmHg)). The product was characterized by the following data: IR (thin film) cm-1 3330 (broad peak), 2945, 2875, 1455, 1440, 1315, 1295, 1265, 1150, 1075, 1060, 1020, 1000, 965, 900, 740, 725, 655; 1H NMR (200 MHz, CDCl3) δ 3.67 (m, 2H), 3.55 (t, J=6.5 Hz, 2H), 1.82 (pentet, J=7 Hz, 2H), 1.4-1.7 (m, 4H), 1.37 (m, 1H); 13C NMR (22.5 MHz, CDCl3) δ 62.4, 45.0, 32.4, 31.9, 23.2; Mass Spectra (70 eV) m/z (relative abundance) 124, 122 (M+, not observed), 106, 104 (M+ - H2O, 0.7, 1.3), 105 (0.5), 93 (7.1), 91 (20.5), 69 (13.7), 68 (100.0), 67 (13.6), 57 (13.4), 56 (41.4), 55 ( 57.0). |
[References]
[1] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4008 - 4017
[2] Synthetic Communications, 1985, vol. 15, # 7, p. 569 - 580
[3] Patent: US5264619, 1993, A
[4] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3361 - 3364
[5] Phosphorus and Sulfur and the Related Elements, 1987, vol. 31, p. 161 - 176 |