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

HRID 1288517Notes

Reaction equation

HRID 1288517 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:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26]>CO>[Cl-:17].[CH3:1][CH:2]([N+:14]([CH3:16])([CH3:15])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])/[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

4

Reactant 2

HCID 72122,4-Dichlorobenzyl chlorideHCID 21502510[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine

Product 1

HCID 21502536[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(2,4-dichlorobenzyl)ammonium chlorideYield 119.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine (2.0 g), α,2,4-trichlorotoluene (3.0 g) and methanol (10 cc) was refluxed for 5 hours, and the solvent of the reaction mixture was distilled off under reduced pressure. The residue was dissolved in a small amount of benzene and thereto was added a large amount of ether. The precipitated oil was gathered by decantation and dissolved in a small amount of benzene and thereto was further added a large amount of ether. The solvent was distilled off to give colorless oil (4.5 g) of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(2,4-dichlorobenzyl)ammonium chloride.

Workup

  1. temperaturewas refluxed for 5 hours
  2. distillationthe solvent of the reaction mixture was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in a small amount of benzene
  4. additionwas added a large amount of ether
  5. dissolutiondissolved in a small amount of benzene
  6. additionwas further added a large amount of ether
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-09e3b92a5f514f1aa2ef29c21c8300f5
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

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