(4-Chlorobutyl)benzene → 1-Heptyl-3-(4-phenylbutyl)imidazolium chloride

HRID 65245Notes

Reaction equation

HRID 65245 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:12]([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CO>[Cl-:1].[CH2:12]([N+:19]1[CH:23]=[CH:22][N:21]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 78543(4-Chlorobutyl)benzeneHCID 1866691-Heptyl-1H-imidazole

Product 1

HCID 231821431-Heptyl-3-(4-phenylbutyl)imidazolium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 5.35 g (0.32 mole) of (4-chlorobutyl)benzene and 5.27 g (0.32 mole) 1-heptyl-1H-imidazole, stir the mixture at approximately 145° C. for about 30 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide 9:1). At the completion of the reaction, dissolve the resulting cooled oil in methanol and evaporate the solvent. Dissolve this product in 125 ml H2O and extract the solution with 5×100 ml hexane. Then extract the aqueous with 2×50 ml methylene chloride. Combine the methylene chloride layers and wash with 1×100 ml saturated aqueous NaCl solution. Dry the methylene chloride extracts over sodium sulfate. Evaporate the solvents to obtain 1-heptyl-3-(4-phenylbutyl)imidazolium chloride as an oil. Dissolve the oil in approximately 35 ml acetone, and to it add an equimolar amount of phthalic acid. Remove the solvents in vacuo to obtain the title compound, which may be recrystallized from acetone.

Workup

  1. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide 9:1)
  2. customAt the completion of the reaction
  3. dissolutiondissolve the resulting
  4. customevaporate the solvent
  5. dissolutionDissolve this product in 125 ml H2O
  6. extractionextract the solution with 5×100 ml hexane
  7. extractionThen extract the aqueous with 2×50 ml methylene chloride
  8. washwash with 1×100 ml saturated aqueous NaCl solution
  9. dry with materialDry the methylene chloride
  10. customEvaporate the solvents

Sources & evidence

ORD record
ord-d9a3111e25374f3aa0502225fb20c990
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

Loading…