Methanol → N,N,N-Trimethyl(3-methylphenyl)methanaminium bromide

HRID 397256Notes

Reaction equation

HRID 397256 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Br:6].[CH3:10][N:11]([CH3:13])[CH3:12].CO>C(OCC)C>[Br-:6].[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N+:11]([CH3:13])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 1146TrimethylamineHCID 12099m-Xylyl bromide

Product 1

HCID 89110N,N,N-Trimethyl(3-methylphenyl)methanaminium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A] 3-Methylbenzyl bromide (24.64 g, 1.33×10−1 mol, Aldrich) is dissolved in 221 g of diethyl ether in a 500 ml round bottomed flask. A 33% (w/w) solution of trimethylamine in methanol (35.80 g, 2.00×10−1 mol, Acros) is added all at once, forming a precipitate almost immediately. The reaction mixture is allowed to stir overnight at room temperature and is then filtered and washed three times with diethyl ether. The resulting powder is dried in a vacuum oven overnight to obtain 3-methylbenzyl trimethylammonium bromide.

Workup

  1. customforming a precipitate almost immediately
  2. filtrationis then filtered
  3. washwashed three times with diethyl ether
  4. customThe resulting powder is dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-b6fe267044114fd3a460303bad8dcd46
Source dataset
uspto-grants-2003_08
Patent number
US06610458B2

Reaction notes

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