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

HRID 1280314Notes

Reaction equation

HRID 1280314 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 bromideYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A] 3-Methylbenzyl bromide (24.64 g, 1.33×10−1 mol, Aldrich) was 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) was added all at once, forming a white precipitate almost immediately. The reaction mixture was allowed to stir overnight at room temperature and was then filtered and washed three times with diethyl ether. The resulting white powder was dried in a vacuum oven overnight to afford 29.38 g (90% yield) of 3-methylbenzyl trimethylammonium bromide.

Workup

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

Sources & evidence

ORD record
ord-bc807ed1690642eea57794986d97e107
Source dataset
uspto-grants-2002_09
Patent number
US06451500B1

Reaction notes

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