Hexane → (2-acetoxyethyl)dodecyloxymethyldimethylammonium Benzoate

HRID 1517218Notes

Reaction equation

HRID 1517218 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].CCCCCC.[CH2:16]([O:28][CH2:29]Cl)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:31]([O-:39])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[K+]>CS(C)=O.C(Cl)(Cl)Cl>[C:31]([O-:39])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[C:1]([O:4][CH2:5][CH2:6][N+:7]([CH2:29][O:28][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:9])[CH3:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8058HexaneHCID 15013Dimethylaminoethyl acetateHCID 12215332Chloromethyl dodecyl etherHCID 23661960Potassium Benzoate

Product 1

HCID 69297233(2-acetoxyethyl)dodecyloxymethyldimethylammonium BenzoateYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
18 °C

Procedure

In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, the 2-(dimethylamino)ethyl acetate (0.05 mol) was mixed with 30 mL of anhydrous hexane. Chloromethyl dodecyl ether (0.055 mol) was slowly added over 5 minutes. After 15 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The precipitate was washed with 30 mL of hexane and used in the next step without further purification. The crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water and aqueous solution of potassium benzoate (0.065 mol) was added. After 30 min, 30 mL of chloroform was added. The chloroform phase was separated and washed with distilled water until chloride ions were no longer detected using AgNO3. The obtained grease was dried under vacuum. The product was obtained as grease in 67% yield. Thermogravimetric analysis: Tonset=122° C. 1H and 13C NMR (DMSO) were obtained.

Workup

  1. customIn a two-necked, round bottomed flask, equipped with a condenser and addition funnel
  2. customthe crude product was separated
  3. washThe precipitate was washed with 30 mL of hexane
  4. customused in the next step without further purification
  5. dissolutionThe crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water
  6. waitAfter 30 min
  7. customThe chloroform phase was separated
  8. washwashed with distilled water until chloride ions
  9. customThe obtained grease was dried under vacuum
  10. customThe product was obtained as grease in 67% yield
  11. customTonset=122° C

Sources & evidence

ORD record
ord-1964d963b41d484383b548897c2d9c04
Source dataset
uspto-grants-2012_07
Patent number
US08232265B2

Reaction notes

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