Salicylic Acid → HCID 178454882, compound

Participants

Reaction Steps

Cinnamic acid (0.7408 g, 5 mmol), salicylic acid (0.6909 g, 5 mmol) and tetrabutylphosphonium hydroxide (˜40% sol. in H2O) (3.414 g, 5 mmol) were dissolved in 20 ml of acetone stirred and for 15 min at room temperature. The solvent was evaporated and the remaining viscous liquid was dried at 0.1 mbar with stirring for 24 hrs. Identity and purity was confirmed via 1H NMR. The desired compound is isolated as a colourless liquid; 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=7.67 (m, 3H), 7.57 (d, J=19.1 Hz, 1H), 7.41 (m, 3H), 7.12 (m, 1H), 6.56 (m, 3H), 2.17 (m, 8H), 14.1 (m, 16.H), 0.91 (t, J=6.9 Hz, 12 H). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=35.1. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=171.2, 167.6, 163.0, 143.3, 134.4, 131.1, 130.0, 129.9, 128.9, 128.1, 120.7, 120.0, 115.7, 115.6, 23.3 (d, J=15.9 Hz), 22.6 (d, 4.2 Hz), 17.3 (47.8 Hz), 13.2 (s). Tg−43° C., T5%onset 191° C.

Provenance & Evidence