Wolff-Kishner reduction, large scale, feasible or just suicide?

[victorplum]

As per title: I was trying to come up with a stereo-selective synthesis, but I'm stuck at one point where I have to remove a carbonyl. Turning it into an alcohol would vanish the selectivity goal. Now, wherever I look for information it's just people warning about preferring any other way is appliable and warning about hydrazine carcinogenic properties (+ keeping it at 200+°C while it's volatile enough even at room temp + boiling KOH solution). Up-scaling it at 100+g scale seems something very few people would do: is there a way to not die? I don't have a lab either, so I can't even do that under a hood (well, it still have to be built, but for budget reasons a hood is usually added only when you need it)

An alternative would be the Clemmensen, but it requires mercury. Really, how could I remove that fucking oxygen without having to write a will just in case?

 

[highTEMPO]

I would not do the wolff-kishner reduction unless you have a proper lab. Hydrazine is rocket fuel. I wouldnt worry about cancer I have a bottle of sand in my lab and it says may cause cancer on the label. In regards to getting rid of the oxygen, you could reduce with raney nickel by first reacting the carbonyl with ethanedithiol, however this reaction can get out of control quickly as well. Good luck

 

[HerrHaber]

This one needs to be scaled up only carefully and progressively... I've seen a successful microwave reaction but I guess you could do several batches at a time and poll the mixtures for the workup, anyway it must be done in small loading of the reactor. Is it a ketone you are trying to to remove?