I'm preparing a hydrazone with beta-cyclocitral and phenyl hydrazine. The product purified through chromotography is oily and always messy on TLC after concentration. Is there any way to purify it through crystalization? My product melts in PE.
By messy do you mean that it stretches out? At least one of nitrogens should be basic, so to get a good TLC in silica gel you would need some tertiary base, like triethylamine (around 1%).
Crystallizing is a tricky thing, you can try minimum volumes of hot ethanol or chloroform, they frequently work for that. Sometimes hexane/petroleum ether is good for mixed solvent crystallization (with ethyl acetate or dichloromethane for primary dissolution). Ratio is unclear, you can judge by tlc, as in final ratio solubility of your product should be poor, but not zero, and hence mobility should be low.
U can Crystallize after solublise under heating condition taking ur pdt in hexane and small amount of EtOAc......
you can try another method with silica gel it would be presence of Dioxane -Acetone (50:50) , may you will help with this and hopefully there is no messy.
also go through layer of aluminia with eluent ethanol
Purification of the hydrazone has been effectively achieved by dissolving hydrazone in dimethyl formamide (DMF)by heating and on cooling crystalline hydrazone separates out in the pure form.
Dear Dong Yi in our hands we occasionally found that recrystallization of oily and highly soluble products can be achieved by using acetonitrile as solvent.
Dong Yi P.S. Sometimes it also helps to triturate (stir) the oily product with cold pentane while stirring with a glass rod. Chances are that this converts the oil into a solid.
Dear Dong Yi it would be interesting to know at some stage if any of the suggestions given here was really helpful.
Oily product may be mixture .To purify hydrazone , triturate an oily product in cold condition with n-hexane and keep it for 24hrs. in freeze.
Dear Dong Yi thank you again for your interesting technical question. I looked up the compound cyclocitral phenylhydrazone in the SciFinder database. The search revealed only one paper in which the p-nitrophenylhydrazone has been reported. A search for the structural formula revealed no match at all, so that I assume that the compound "cyclocitral phenylhydrazone" has not yet been described in the chemical literature. In general, I agree with Mikhail Nekrasov in that ethanol should be a suitable solvent for recrystallization of your compound. I found a number of related phenylhydrazine derivatives (e.g. citral phenylhydrazone) which were purified by recrystallization from hot ethanol. By the way, your question has been asked quite a while ago and has received a number of potentially useful answers. It is a good habit on this platform to recommend useful answers.
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