Hi, today I want to have a look at the reaction which is shielding Benzaldehyde and the dissimilar reaction. This has been recommended to me by Eric M, so thanks mate. So with this let's dry chlorine and shorter chlorination time, which is a plus, but on the other hand it requires hexamene which is maybe quite exotic reagent in the US, I don't know. So I bought these hexamene tablets, you can buy them from armyshops or some survival stuff. I'm not sure if armyshops are thinking the US. I didn't do proper research before I was doing this reaction, so I later found out that there is quite a bit of trioxane in these tablets. But fortunately if you look at the hexamene data, you can see that it has quite low solubility in quite available solvents. In fact, that's the only slowest one. And here on this page you can see that the trioxane is readily solvable in acetone, whatever that means. I just measured about 150 grams of these tablets and these of them in about 250 ml of water. So I left these on the hot plate for about like hour or so. Just covered it up so I don't lose too much water. I had a stir bar there but it wasn't really necessary to have it there because it doesn't really help too much. You could clearly see that the solution was saturated but it doesn't really want to crystallize. So I'm not really sure if you can purify this by recrystallization. After everything has dissolved, I decanted the solution. You can clearly see that there was some junk in the tablets. I guess it looks like sand, it feels like sand, probably sand. To dissect some installation I will add 75 ml of benzoyl chloride. Then start stirring and reflux for a few hours. Everything really happened initially but as the water started to reach boiling point it started to go a little bit crazy but it wasn't anything really terrible. It just looked a little bit more vigorous. After whole thing calm down a little bit, you could see distinct layers and over the period of 40 minutes or so the aqueous layer went from milkyclar to clear. And nothing exciting really happened and I returned to this reaction after about 4 or 5 hours of total run time. The organic layer looked red and the aqueous layer started to look milky again. There are some crystals in the condenser and this is probably hexamene and it is because initially when the thing erupted a little bit it threw a lot of vapor up there so here I'm separating the organic layer. We don't really have to do this, you could run a whole reaction in one flask. I only have 500 ml of lm and you need to neutralize all the amines and then a bunch of another hydrochloric acid to hydrolyze benzoyl chloride that is definitely there but in unknown concentrations. So this is the organic layer. It's mostly benzoyldehyde, probably a bunch of metilamine and benzoyl chloride. So we can add hydrochloric acid that will form salt with metilamine and this can be washed away with water. And the rest of hydrochloric acid we can use to hydrolyze the benzoyl chloride. So I will add about 150 ml of hydrochloric acid now and you can see that the amines are immediately reacting with hydrochloric acid to form really thick fog and you can now reflux this and then distill off the benzoyldehyde. But for some reason I have decided that no, I don't believe this. I am going to distill benzoyldehyde right now with all its impurities and then I will be doing hydrolysis separately. I guess it's not bad because then I had really clear product and I really mean not yellow and then I can see what happens. Now after this distillation I can really see that I have lost about one third of the product so that it's about 25 ml which is not that bad if you consider that I have refluxed this for about 4 hours in atmosphere but you can already see color change in first 40 minutes. And this is after about 4 hours. Well it looks fairly processed so I hope there won't be any impurities after distillation. So again I separate the organic layer. Then I added a bunch of clean water and to neutralize hydrochloric acid unfortunately I had to use calcium carboneid because I did not have anything else. But I guess it works so why not, right? And finally I distill the benzoyldehyde. During distillation I took about 100 nanogram sample and I put it into machine for analysis. The machine said that it tastes very spicy, almost not aromatic at all and also smell was very spicy. There's definitely quite a lot of benzoyldehyde but there's some impurity that really is overwhelming for all my senses so I cannot really get rid of it. Well in any case I separated benzoyldehyde again, that is the bottom organic layer. You can see that there's a lot less than we had initially. Then I dried the benzoyldehyde with calcium sulfate. It's just such a shame that I forgot to dry my bottle before I did this, right? And finally I got about 18 ml of benzoyldehyde. Now that doesn't mean that this melted sucks because obviously I did this on purpose, just to see if I can get rid of the impurity that I saw in this sample. And unfortunately I can't. I put this benzoyldehyde sample in the freezer just to see if something will crystallize out and long and behold we have some crystals. The temperature is about –25 degrees Celsius. This is not benzoyldehyde because it will melt and it's not really benzoyl chloride I think because I mean it smells really just like the sample itself, the benzoyldehyde sample. But even after I filtered these crystals the benzoyldehyde smell was really just awful. It wasn't good at all. This freezing and filtering took me about hour and when I checked the gradually cylinder that I had benzoyldehyde in, you can see these crystals. There's no liquid there and ambient temperature is about 10 degrees Celsius so the oxidation rate is quite impressive. Now last thing I can do I guess is vacuum distillation to see if I can get rid of this impurity and unfortunately this did not help at all. I mean it kinda says that I cannot present you a process that works perfectly well but at least you can see where things can fail. And who knows maybe on the sixth time I can get it right but I cannot really tell in advance so here's the video of what I have now. Okay so this is about everything I have for now so see you later.