Okay so…
Today I decided I wanted to do a Henry condensation, this time on 3,4,5-TMOBA.
So I figured, why not start with Shulgin’s method - only I didn’t really want to commit to 20g of aldehyde and so I halved everything.
I was super surprised that after around 1.5h it started getting pretty dark - certainly darker than the orange that is shown in the video tutorial on here - I know they used even more nitromethane than shulgin but still.
So it first of all didn’t look like it was going to precipitate out of solution on its own and iv been doing this reaction with 2,5-DMOBA recently and that’s been using methanol as a solvent - so I sort of forgot I was using nitromethane and added some water to it.
Anyway it obviously just formed a layer on top and so I added it to a sep funnel and got rid of it but basically as soon as I did that it started to precipitate out…
Im guessing that some of the nitromethane was pulled into the water meaning that the solubility of the nitrostyrene in the rest of the solvent decreased and it started to precip?
I used 10g of the aldehyde, 20ml of nitromethane and 0.5g of ammonium acetate…
I ran TLC at just before the 2 hour mark and it seemed to have fully converted so I pulled it early.
Anyway I’ll filter it tomorrow, it’s too late to run my pump now but yeh I’ll post photo’s tomorrow.
Honestly this was really just a test but it’s got me wanting to run it again only following the video tutorial and also with nitroethane this time.
I am basically making a few different b-nitrostyrene’s as well as nitropropenes to take somewhere safer than here to reduce using LAH…then I can try the NaBH + catalyst synthesis.
It was just weird how it precipitated out in the end…that’s all
Today I decided I wanted to do a Henry condensation, this time on 3,4,5-TMOBA.
So I figured, why not start with Shulgin’s method - only I didn’t really want to commit to 20g of aldehyde and so I halved everything.
I was super surprised that after around 1.5h it started getting pretty dark - certainly darker than the orange that is shown in the video tutorial on here - I know they used even more nitromethane than shulgin but still.
So it first of all didn’t look like it was going to precipitate out of solution on its own and iv been doing this reaction with 2,5-DMOBA recently and that’s been using methanol as a solvent - so I sort of forgot I was using nitromethane and added some water to it.
Anyway it obviously just formed a layer on top and so I added it to a sep funnel and got rid of it but basically as soon as I did that it started to precipitate out…
Im guessing that some of the nitromethane was pulled into the water meaning that the solubility of the nitrostyrene in the rest of the solvent decreased and it started to precip?
I used 10g of the aldehyde, 20ml of nitromethane and 0.5g of ammonium acetate…
I ran TLC at just before the 2 hour mark and it seemed to have fully converted so I pulled it early.
Anyway I’ll filter it tomorrow, it’s too late to run my pump now but yeh I’ll post photo’s tomorrow.
Honestly this was really just a test but it’s got me wanting to run it again only following the video tutorial and also with nitroethane this time.
I am basically making a few different b-nitrostyrene’s as well as nitropropenes to take somewhere safer than here to reduce using LAH…then I can try the NaBH + catalyst synthesis.
It was just weird how it precipitated out in the end…that’s all