Ethyl Bromide → [1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylethylammonium bromide

HRID 1288513Notes

Reaction equation

HRID 1288513 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].[CH2:17]([Br:19])[CH3:18]>>[Br-:19].[CH3:1][CH:2]([N+:14]([CH3:16])([CH3:15])[CH2:17][CH3:18])/[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

3

Reactant 2

HCID 6332Ethyl BromideHCID 21502510[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine

Product 1

HCID 21502542[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylethylammonium bromideYield 26.2%

Procedure

A mixture of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine (2.3 g) and ethylbromide (6.0 g) was refluxed for 3 hours, and then the excess ethylbromide was distilled off. The residue was recrystallized from a mixed solvent of benzene and ether to give colorless crystals (0.9 g) of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylethylammonium bromide.

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationthe excess ethylbromide was distilled off
  3. customThe residue was recrystallized from a mixed solvent of benzene and ether

Sources & evidence

ORD record
ord-b54540336f714b4a9f2968760440f697
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

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