[Synthesis]
Cyclopentadiene was mixed with acryl alcohol in a pressure reactor at a molar ratio of 1:2.4 and the reaction was carried out at 170-180 °C and a pressure of 4-5 atm to give 5-norbornene-2-methanol. The product had a yield of 74%, a boiling point of 82-83 °C (10 mmHg), a refractive index nD20 of 1.4970, and a density d420 of 1.027 g/cm3. IR spectra showed characteristic absorption peaks: 3500 cm?1 (OH stretching vibration), 2930-2895 cm?1 and 2880-2830 cm?1 (C-H stretching vibration), 1200 -1100 cm?1 (C-O stretching vibration).1H NMR spectral data (δ, ppm; J, Hz): 0.45 (1H, H6exo, dd, J = 4.1, 13.4), 1.19 (1H, H7anti, t, J = 7.9), 1.44 (1H, H6endo, t, J = 4.1), 1.68-1.72 (1H , H7syn, m), 2.86 (1H, H5, m), 3.29 (1H, H4, m), 3.36-3.46 (2H, C8H2, m), 3.46 (1H, H1, ddd, J = 4.4, 4.6, 4.8), 3.92 (1H, OH, br s), 6.00-6.08 (2H, H2, H3, m).13C NMR spectral data (δC, ppm): 28.8 (C6), 41.8 (C5), 42.3 (C1), 43.6 (C4), 49.4 (C7), 65.8 (C8), 132.3 (C3), 137.8 (C2). |
[References]
[1] Petroleum Chemistry, 2000, vol. 40, # 4, p. 272 - 274
[2] Russian Journal of General Chemistry, 2018, vol. 88, # 10, p. 2204 - 2208
[3] Zh. Obshch. Khim., 2018, vol. 88, # 10, p. 1718 - 1722,5
[4] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951
[5] Russian Journal of Applied Chemistry, 2008, vol. 81, # 10, p. 1803 - 1807 |