Ethanol → [1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(3,4-dichlorobenzyl)ammonium iodide

HRID 1288516Notes

Reaction equation

HRID 1288516 reaction equation
[CH3:1][CH:2]([N:14]([CH3:16])[CH3:15])/[CH:3]=[CH:4]/[CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH:7]=[C:6]1[CH3:13].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1.C(O)C.[I-:30].[K+]>CO>[I-:30].[CH3:1][CH:2]([N+:14]([CH3:16])([CH3:15])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)/[CH:3]=[CH:4]/[CH:5]1[C:10]([CH3:11])([CH3:12])[CH2:9][CH2:8][CH:7]=[C:6]1[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 4875Potassium IodideHCID 76093,4-Dichlorobenzyl chlorideHCID 21502510[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine

Product 1

HCID 21502455[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(3,4-dichlorobenzyl)ammonium iodideYield 58.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine (3.0 g) and α,3,4-trichlorotoluene (4.0 g) in methanol (15 cc) was refluxed for 2 hours, and thereto were added ethanol (40 cc) and then an aqueous solution of potassium iodide (3.0 g). The solvent of the reaction mixture was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of methanol and ether to give colorless crystals (4.0 g) of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(3,4-dichlorobenzyl)ammonium iodide, m.p. 160°-165° C.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. customthe residue was recrystallized from a mixed solvent of methanol and ether

Sources & evidence

ORD record
ord-927feb84fa774fb38630b6dedbe4443f
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

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