p-Toluenesulfonic acid → HCID 86612076, compound

HRID 2403133Notes

Reaction equation

HRID 2403133 reaction equation
[Cl-].[CH2:2]([N+:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:14])[CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.[OH-].[Na+]>O>[C:25]1([CH3:35])[CH:26]=[CH:27][C:28]([S:31]([O-:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH2:15]([N+:12]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:14])[CH3:13])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 23558Didecyldimethylammonium Chloride

Product 1

HCID 86612076HCID 86612076, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

0.015 mol of didecyldimethylammonium chloride, 0.01 mol of p-toluenesulfonic acid, 0.01 mol of NaOH and 100 mL of distilled water were charged to a round bottomed flask and heated. The mixture was stirred for 2 h at 40° C., whence the phases were allowed to separate. The organic layer was then washed three times with distilled water. The aqueous phases were tested for the presence of chloride ion using silver nitrate solution. Finally, the organic layer was vacuum stripped to remove water. The obtained didecyldimethylammonium p-toluenesulfonate with 95% yield is soluble in chloroform, acetone, DMSO, and insoluble in water and hexane.

Workup

  1. temperatureheated
  2. customto separate
  3. washThe organic layer was then washed three times with distilled water
  4. customto remove water

Sources & evidence

ORD record
ord-3638d7af84534c07bb0fba6d3fe28f13
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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