Salicylic Acid → HCID 178454882, Verbindung

HRID 921993

Reaktionsgleichung

Reaktionsgleichung von HRID 921993
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 178454882HCID 178454882, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f4b78963b5684d3d9d33ffbc1b7686c4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278134B2

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