Synthesis of Tetrapropylammonium (Z)-12-Hydroxyoctadec-9-enoate (TPA-RA)
Quantities of substrates taken: Sodium ricinoelate (1g, 0.0031 mol), TPA-Br (1g, 0.0037 mol), yield obtained 86% (1.24 g).1H NMR (CDCl3, ppm): δ 5.54 (m, -CH=CH-), 5.38 (m, -CH=CH-), 3.60 (m, 1H, -CHOH), 3.27(m, 8H,-CH2N), 2.20 (t, 2H, -H2CCOO), 2.19 (t, 2H, -CH2-C=C-), 2.02 (t, 2H, -CH2-C=C-), 1.73 (m, 8H, 4xCH2), 1.56 (m, 2H, -CH2), 1.44 (m, 2H, -CH2), 1.33 (m, 4H, 2xCH2), 1.27 (m, 12H, 6x-CH2), 1.03 (m, 12H, 4x-CH3), 0.87 (t, 3H, CH3). 13C NMR (CDCl3, ppm): δ 177.3, 132.4, 125.1, 71.3, 58.6, 36.6, 31.8, 35.2, 29.6, 25.5, 22.7, 15.7, 14.1, 13.5. IR (CHCl3, cm-1): 3346, 3005, 2922, 2854, 1709, 1554, 1451, 1151, 731.