Salicylic Acid → HCID 178454882, compound

HRID 921993

Reaction equation

HRID 921993 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]([OH:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].[OH-].[CH2:23]([P+:27]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>CC(C)=O>[C:12]([O-:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].[CH2:36]([P+:27]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38][CH3:39].[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 87842-Propenoic acid, 3-phenyl-HCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 178454882HCID 178454882, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  1. customThe solvent was evaporated
  2. customthe remaining viscous liquid was dried at 0.1 mbar
  3. stirringwith stirring for 24 hrs

Sources & evidence

ORD record
ord-f4b78963b5684d3d9d33ffbc1b7686c4
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

Loading…