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

HRID 431416Notes

Reaction equation

HRID 431416 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-fb66ff3dd7d94083bd0931e94fa42251
Source dataset
uspto-grants-2003_12
Patent number
US06660449B2

Reaction notes

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