Chloroform → Didecyldimethylammonium trans-Cinnamate

HRID 2403116

Reaction equation

HRID 2403116 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.[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]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 16958DidecyldimethylammoniumHCID 444539Cinnamic Acid

Product 1

HCID 67382645Didecyldimethylammonium trans-CinnamateYield 93%

Reagents, catalysts & solvents 2

HCID 16957Didecyl dimethyl ammonium bromideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-659bb189dd2e4f7cbfb156ff5dd61d0a
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Linked notes

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