Ethanol → HCID 21502441, compound

HRID 1288523Notes

Reaction equation

HRID 1288523 reaction equation
[Br-].[CH3:2][CH:3]([N+:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][Br:18])/[CH:4]=[CH:5]/[CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14].[I-:21].[K+].C(O)C>O>[I-:21].[CH3:2][CH:3]([N+:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][Br:18])/[CH:4]=[CH:5]/[CH:6]1[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 4875Potassium IodideHCID 21502437HCID 21502437, compound

Product 1

HCID 21502441HCID 21502441, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(2-bromoethyl)ammonium bromide (1 g) and potassium iodide (0.54 g) in a mixed solvent of ethanol (5 cc) and water (5 cc) was stirred for 30 minutes at room temperature, and the reaction mixture was concentrated under reduced pressure. The residue was extracted with chloroform, and the solvent of the chloroform layer was distilled off. To the residue was added benzene, and the benzene layer was concentrated to dryness. The residue was recrystallized from a mixed solvent of acetonitrile and ether to give orange crystals (1.0 g) of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(2-bromoethyl)ammonium iodide, m.p. 149°-151° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with chloroform
  3. distillationthe solvent of the chloroform layer was distilled off
  4. additionTo the residue was added benzene
  5. concentrationthe benzene layer was concentrated to dryness
  6. customThe residue was recrystallized from a mixed solvent of acetonitrile and ether

Sources & evidence

ORD record
ord-337f62912a0c43f896a8bdaca1a6ecb8
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

Loading…