The Conversion of α,ω-Diols into Mono Iodo Alcohols

References

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• Entry 1. 3-Iodopropanol. Bp3. 47°C. NMR:9 δ 1.81 (m, 1H, -OH), 2.05 (t of t, 2H, J = 6.7 and 6.5 Hz, -CH2-), 3.31 (t, 2H, J = 6. 7 Hz, -CH21), 3.74 (t, 2H, J = 6.5 Hz, -CH-2OH). MS:8 186 (M+, 9.6%), 59 (M+-I, 100%). Entry 2. 4-Iodobutanol. Bp3. 72°C. NMR: δ 1.96 (m, 1H, -OH), 1.68 (t of t, 2H, J = 6.3 and 7.5 Hz, -CH-2CH2OH), 1.94 (t of t, 2H, J = 6.9 and 7.5 Hz, -CH-2CH2I), 3.24 (t, 2H, J = 6.9 Hz, -CH2I), 3.69 (t, 2H, J = 6.3 Hz, -CH-2OH). MS: 200 (M+, 0.5%), 183 (M+-OH, 10%), 73 (M+-I, 75%), 55 (C4H7 +, 100%). Entry 3. 3-Hydroxy-1-iodobutane. Bp3. 63°C. NMR: δ 1.24 (d, 3H, J = 6.9 Hz, CH3-), 1.95 (m, 2H, -CH2-), 3.31 (t, 2H, J = 6.8 Hz, -CH2I), 3.79 (m, 1H, -CHOH-), 4.30 (m, 1H, -OH). MS: 200 (M+, 2.3%), 27 (I+, 47%), 73 (M+- I, 100%). Entry 4. 5-Iodopentanol. Bp3. 81°C. NMR: δ 1.52 (m, 4H, HOCH2-CH-2-CH-2-), 1.82 (t of t, 2H, J = 6.8 and 7.2 Hz, -CH-2-CH2I), 2.30 (m, 1H, -OH), 3.16 (t, 2H, J = 6.8 Hz, -CH2I), 3.59 (t, 2H, J = 6.1 Hz, -CH-2OH). MS: 214 (M+, 0.2%), 197 (M+-OH, 0.2%), 127 (I+, 4.4%), 87 (M+-I, 27%), 41 (C3H5 +, 100%). Entry 5. 6-Iodohexanol. Bp3. 90°C. Mp. -8°C. NMR: δ 1.45 (m, 6H, -(CH2)3), 1.81 (t of t, 2H, J = 6.8 and 7. 1 Hz, -CH-2-CH2I) 2.48 (m, 1H, -OH), 3.21 (t, 2H, J = 6.8 Hz, -CH2I), 3.62 (t, 2H, J = 6.2 Hz, -CH-2OH). MS: 228 (M+, 0.1%), 211 (M+-OH, 18%), 155 (C2H4I+, 17%), 127 (I+, 6%), 101 (M+-I, 11%)
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• The infrared spectra9 are quite similar for all iodo alcohols. Some characteristic absorptions are: 3340 (OH), 2932 and 2856 (CH2), 1452 and 1425 (CH2), 1205 and 1168 (COH), 1055 (CO) and 595 and 495 cm−1 (CH2I)
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• In the case of 1,6-hexanediol (entry 5) the solution was kept at reflux temperature
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• LKB 2091–2130 system, operating at 22 eV, 25 uA. Equipped with a 30 m WCOT. UV-17 column operating at 147°C (injection port 180°, septum 170°) with a split injection system
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• 1H NMR spectra were obtained in CDC13 solution on a Bruker WM 300 instrument. IR spectra were recorded on a Perkin-Elmer 580 infrared spectrometer
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