Hexane → (2-acetoxyethyl)heptyloxymethyldimethylammonium Benzoate

HRID 2403121Notes

Reaction equation

HRID 2403121 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14]C.[CH2:16]([O:22][CH2:23]Cl)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CS(C)=O>[C:1]([O-:4])(=[O:3])[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:1]([O:4][CH2:5][CH2:6][N+:7]([CH2:23][O:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:10])([CH3:9])[CH3:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 15013Dimethylaminoethyl acetateHCID 125465121-(Chloromethoxy)hexane

Product 1

HCID 69294144(2-acetoxyethyl)heptyloxymethyldimethylammonium BenzoateYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
18 °C

Procedure

In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, 2-(dimethylamino)ethyl acetate (0.1 mol) was mixed with 150 mL of anhydrous hexane. Chloromethyl hexyl ether (0.1 mol) was slowly added over 15 minutes. After 30 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The crude product was washed with 100 mL of hexane and used in the next step without further purification. The material was dissolved in 100 mL of water and aqueous solution of sodium benzoate was added in stoichiometric amount. After 30 minutes, two phases were separated. The water phase was removed and 100 mL of anhydrous acetone was added to the residue. Precipitated NaCl was filtered off and the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum. The product was obtained as viscous liquid in 65% yield. Thermogravimetric analysis: Tonset=120° 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 crude product was washed with 100 mL of hexane
  4. customused in the next step without further purification
  5. dissolutionThe material was dissolved in 100 mL of water
  6. additionaqueous solution of sodium benzoate was added in stoichiometric amount
  7. waitAfter 30 minutes
  8. customtwo phases were separated
  9. customThe water phase was removed
  10. addition100 mL of anhydrous acetone was added to the residue
  11. filtrationPrecipitated NaCl was filtered off
  12. dry with materialthe obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum
  13. customThe product was obtained as viscous liquid in 65% yield
  14. customTonset=120° C

Sources & evidence

ORD record
ord-9f4d80c053d7406fb87faeb782e8c414
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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