Benzalkonium → Benzalkonium trans-Cinnamate

HRID 2403117

Reaction equation

HRID 2403117 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:16])[CH3:15].[Cl-].[C:25]([OH:35])(=[O:34])/[CH:26]=[CH:27]/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCCCCCCCCCCCC[N+](CC1C=CC=CC=1)(C)C.C(Cl)(Cl)Cl>CS(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:16])[CH3:15].[C:25]([O-:35])(=[O:34])/[CH:26]=[CH:27]/[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 2330BenzalkoniumHCID 6212ChloroformHCID 444539Cinnamic AcidHCID 3014024Benzalkonium Chloride

Product 1

HCID 86612073Benzalkonium trans-CinnamateYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Benzalkonium chloride (0.001 mol) was dissolved in warm distilled water. trans-Cinnamic acid (0.001 mol) was added to the benzalkonium solution. The reaction solution was stirred at 90° C. for 4 hours. The reaction solution was cooled to room temperature 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 an orange viscous liquid was obtained in 90% yield. 1H and 13C NMR (DMSO) were obtained. Melting point (hot plate apparatus)=liquid at room temperature.

Workup

  1. temperaturein warm
  2. distillationdistilled water
  3. temperatureThe reaction solution was cooled to room temperature
  4. customThe two phases were separated
  5. washthe chloroform phase was washed several times
  6. temperaturewith cool
  7. distillationdistilled water
  8. customto remove any inorganic salt
  9. customA rotary evaporator
  10. customremoved the chloroform
  11. customan orange viscous liquid was obtained in 90% yield
  12. customat room temperature

Sources & evidence

ORD record
ord-da1817bee8b748d48d7d816f024c4ed6
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Linked notes

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