Ethanol → Triethylammonium undecylenyl iodide

HRID 2399694Notes

Reaction equation

HRID 2399694 reaction equation
[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C(O)C.[CH2:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17].C(OCC)C>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:16]([NH+:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 1111946211-Iodoundec-1-ene

Product 1

HCID 19383009Triethylammonium undecylenyl iodideYield 61.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Undecylenyl iodide (15 grams), ethanol (120 milliliters), and triethylamine (55 grams) were added to a 500 milliliter round bottom flask equipped with a reflux condenser and a mechanical stirrer. The mixture was boiled at reflux for 46 hours. Solvent was then removed using a rotary evaporator and the residue was treated with diethyl ether and hexane to yield a brown-yellow solid. The solid dissolved in toluene was treated with diethyl ether and hexane to yield a light yellow powder. After isolation by filtration and washing with diethyl ether, the powder was dried in vacuum to yield the product, triethylammonium undecylenyl iodide (12.5 grams), which was identified by 13C NMR spectrometry.

Workup

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureat reflux for 46 hours
  3. customSolvent was then removed
  4. customa rotary evaporator
  5. additionthe residue was treated with diethyl ether and hexane
  6. customto yield a brown-yellow solid
  7. customto yield a light yellow powder
  8. filtrationAfter isolation by filtration
  9. washwashing with diethyl ether
  10. customthe powder was dried in vacuum

Sources & evidence

ORD record
ord-29604cd42c034067a95b696bc97caeb9
Source dataset
uspto-grants-1995_09
Patent number
US05451483

Reaction notes

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