Salicylic Acid → HCID 178421851, Verbindung

HRID 921991

Reaktionsgleichung

Reaktionsgleichung von HRID 921991
[C:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[C:16]([OH:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[OH-].[CH2:27]([P+:31]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>CC(C)=O>[C:16]([O-:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[CH2:40]([P+:31]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:41][CH2:42][CH3:43].[C:1]12([CH2:11][S:12]([OH:15])(=[O:13])=[O:14])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3]

Komponenten

5

Edukt 3

HCID 338Salicylic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Produkt 1

HCID 178421851HCID 178421851, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Camphorsulphonic acid (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 and stirred for 15 min at room temperature. The solvent was evaporated and the remaining viscous liquid was dried at 0.01 mbar with stirring for 24 hrs. The desired compound is isolated as a colourless liquid; 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=7.79 (dd, J1=7.9 Hz, J2=1.8 Hz), 7.52 (m, 1H), 6.94 (m, 3H), 2.97 (d, J=14.8 Hz, 1H), 2.71 (quin, J=10.8 Hz, 1H), 2.36 (d, J=14.8 Hz, 1H), 2.19 (m, 9H), 1.93 (t, J=4.5 Hz, 1H), 1.84 (m, 2H), 1.42 (m, 16 H), 1.26 (m, 2H), 1.05 (s, 3H), 0.91 (t, J=6.9 Hz, 12H), 0.74 (s, 3H). Tg−33° C., T5% onset 203° C.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe remaining viscous liquid was dried at 0.01 mbar
  3. stirringwith stirring for 24 hrs

Quellen und Nachweise

ORD-Eintrag
ord-1bde020c738d42c4b21995a3b4aab939
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278134B2

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