i have attempted different ways which all were unsuccessful or lead to a pasty substance. I have tried imidazole + NaOH in water enthanol mixture, and also imidazole + NaOH in DMSO. and also ethanol.
You can use the following procedure for the synthesis of 1-allyimidazole:
260 ml of 50% strength sodium hydroxide solution, 102 g (1.5 mol) of imidazole and 16.2 g (0.15 mol) of 1-allylimidazole were introduced into a 1 1 four-neck flask with stirrer, thermometer, dropping funnel and reflux condenser, and 126.2 g (1.65 mol) of allyl chloride were added dropwise with vigorous stirring over the course of one hour so that the temperature remained below 40.degree. C. (cooling occasionally with a water bath). After the addition was complete, the mixture was stirred at 40.degree. C. for 30 min. and then diluted with 350 g of water in order to dissolve the salts completely. The organic phase was then separated off, the aqueous phase was extracted with chloroform, and the combined organic phases were dried over sodium sulfate. Removal of the chloroform was followed by distillation under reduced pressure. 165.3 g of GC-pure 1-allylimidazole (yield 149 g (92%) after subtraction of the product employed as catalyst) of boiling point 90.degree.-92.degree. C. under 10 mbar were obtained.
Better use some allyl chloride to promote allynation, this chloride u can seperate after reaction completion, and use always aprotic solvents for imidazoline.
This compound is cheap as chips, why not buying it: Acros - 25g less than $50!
Now chemistry: Try NaHCO3 in methanol at RT, should do it.
Good luck
In supporting informations of the following article (Org. Lett., 2002, 4 (24), pp 4345–4348; DOI: 10.1021/ol0270024) you'll find protocol.
Good luck!!!
You can use the following procedure for the synthesis of 1-allyimidazole:
260 ml of 50% strength sodium hydroxide solution, 102 g (1.5 mol) of imidazole and 16.2 g (0.15 mol) of 1-allylimidazole were introduced into a 1 1 four-neck flask with stirrer, thermometer, dropping funnel and reflux condenser, and 126.2 g (1.65 mol) of allyl chloride were added dropwise with vigorous stirring over the course of one hour so that the temperature remained below 40.degree. C. (cooling occasionally with a water bath). After the addition was complete, the mixture was stirred at 40.degree. C. for 30 min. and then diluted with 350 g of water in order to dissolve the salts completely. The organic phase was then separated off, the aqueous phase was extracted with chloroform, and the combined organic phases were dried over sodium sulfate. Removal of the chloroform was followed by distillation under reduced pressure. 165.3 g of GC-pure 1-allylimidazole (yield 149 g (92%) after subtraction of the product employed as catalyst) of boiling point 90.degree.-92.degree. C. under 10 mbar were obtained.
- Badges
- Science method
- Similar topics
- Chemistry, Organic
- Synthesis