1-(4-Bromobutyl)-4-methoxybenzene → 1-Heptyl-3-[4-(4-methoxyphenyl)butyl]-2,4,5-trimethylimidazolium bromide

HRID 1380360Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[CH2:14]([N:21]1[C:25]([CH3:26])=[C:24]([CH3:27])[N:23]=[C:22]1[CH3:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O>[Br-:1].[CH2:14]([N+:21]1[C:25]([CH3:26])=[C:24]([CH3:27])[N:23]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:22]=1[CH3:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 125 °C

Procedure

Add 3.23 g (0.0133 mole) of 1-(4-bromobutyl)-4-methoxybenzene to 2.77 g (0.0133 mole) of 1-heptyl-2,4,5-trimethyl-1H-imidazole and heat at 125° C. for two hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5). At the completion of the reaction, dissolve the cooled reaction mixture in 100 ml water and then wash with 100 ml cyclohexane. Extract aqueous layer with 150 ml methylene chloride and evaporate to provide the title compound.

Workup

customthe progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5)
customAt the completion of the reaction
dissolutiondissolve
washwash with 100 ml cyclohexane
customExtract aqueous layer with 150 ml methylene chloride and evaporate

Sources & evidence

ORD record: ord-32ab124ef15448b283d7054dda17931c
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581370

Reaction notes

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