Methanol → N,N-Dibutyl-N-[(4-methylphenyl)methyl]butan-1-aminium chloride
Reaction equation
[CH2:1]([N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].CO.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Cl:22])=[CH:19][CH:18]=1.O>C1(C)C=CC=CC=1>[Cl-:22].[CH2:10]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:21][C:20]1[CH:23]=[CH:24][C:17]([CH3:16])=[CH:18][CH:19]=1)[CH2:11][CH2:12][CH3:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Into a 3 l round bottom flask, 176.5 g of tri-n-butylamine and 200 ml of methyl alcohol were charged and heated to 65° C. with stirring. Then, 134.1 g of p-methylbenzyl chloride was added thereto over a period of one hour. Then, this solution was stirred at 65° C. for 10 hours. The heating was stopped, and the solution was cooled to 30° C. Then, 1113 ml of water and 82.4 g of toluene were added thereto, and the mixture was stirred at 30° C. for 30 minutes. Then, the toluene layer was removed to obtain an aqueous solution of tri-n-butyl-p-methylbenzylammonium chloride. To this aqueous solution, 0.3 g of NaHCO3 was added to adjust the pH to 6.8.
Workup
- stirringThen, this solution was stirred at 65° C. for 10 hours
- temperaturethe solution was cooled to 30° C
- stirringthe mixture was stirred at 30° C. for 30 minutes
- customThen, the toluene layer was removed
Sources & evidence
- ORD record
- ord-e9f6b1dd697d439f99761a6a5b91696b
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05545502
Reaction notes
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