Chloroform → Didecyldimethylammonium trans-Cinnamate

HRID 1517213

Reaktionsgleichung

Reaktionsgleichung von HRID 1517213
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:12]([N+:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH3:24])[CH3:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(Cl)(Cl)Cl>[Br-].C([N+](CCCCCCCCCC)(C)C)CCCCCCCCC.CS(C)=O>[C:1]([O-:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH2:25]([N+:22]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:24])[CH3:23])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 16958DidecyldimethylammoniumHCID 444539Cinnamic Acid

Produkt 1

HCID 67382645Didecyldimethylammonium trans-CinnamateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16957Didecyl dimethyl ammonium bromideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Didecyldimethylammonium bromide (0.001 mol) was dissolved in 50 mL of hot distilled water. trans-Cinnamic acid (0.001 mol) was added to the didecyldimethylammonium solution. The reaction solution was stirred at 90° C. for 4 h. The reaction solution was cooled to room temperature and then 60 mL of chloroform was added. The two phases were separated and the chloroform phase was washed several times with cool distilled water to remove any inorganic salt. The presence of chloride anions was monitored by silver nitrate test. A rotary evaporator removed the chloroform and a wax was obtained in 93% yield. 1H and 13C NMR (DMSO) were obtained. Melting point (hot plate apparatus)=54-55° C.

Aufarbeitung

  1. distillationof hot distilled water
  2. temperatureThe reaction solution was cooled to room temperature
  3. customThe two phases were separated
  4. washthe chloroform phase was washed several times
  5. temperaturewith cool
  6. distillationdistilled water
  7. customto remove any inorganic salt
  8. customA rotary evaporator
  9. customremoved the chloroform
  10. customa wax was obtained in 93% yield
  11. customMelting point (hot plate apparatus)=54-55° C.

Quellen und Nachweise

ORD-Eintrag
ord-07bc9591767e4647ad69c355dd98f823
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232265B2

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