Benzyl Chloride → N-(2-Acryloyloxyethyl)-N-benzyl-N,N-dimethylammonium chloride

HRID 1377386Notes

Reaction equation

HRID 1377386 reaction equation
[C:1]([O:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])(=[O:4])[CH:2]=[CH2:3].COC1C=CC(O)=CC=1.[CH2:20]([Cl:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[Cl-:27].[C:1]([O:5][CH2:6][CH2:7][N+:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:10])[CH3:9])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 90154-MethoxyphenolHCID 171112-(Dimethylamino)ethyl acrylate

Product 1

HCID 162073N-(2-Acryloyloxyethyl)-N-benzyl-N,N-dimethylammonium chloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a two-necked flask provided with a reflux condenser and a dropping funnel were introduced 85.9 g (0.6 mol) of acryloyloxyethyl-N,N-dimethylamine, 160 g of acetone and 0.1 g of hydroquinone monomethyl ether, which was employed as a polymerization inhibitor, and then mixed homogeneously. After dropping 75.9 g (0.6 mol) of benzyl chloride thereinto within about 15 minutes, the mixture was allowed to stand overnight under stirring at room temperature. Then the reaction mixture was washed with 500 ml of acetone to obtain crystals of acryloyloxyethyl-N,N-dimethylbenzylammonium chloride.

Workup

  1. customInto a two-necked flask provided with a reflux condenser and a dropping funnel
  2. additionmixed homogeneously
  3. waitto stand overnight
  4. washThen the reaction mixture was washed with 500 ml of acetone

Sources & evidence

ORD record
ord-9092e4df4d9b422faa602ffa715d9309
Source dataset
uspto-grants-1997_09
Patent number
US05665348

Reaction notes

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