Making Benzaldehyde From Cinnamon Oil

Today we are carrying out a super inefficient synthesis of benzaldehyde. This is a cool example of the Retro-Aldol reaction. This really is not a great way to get benzaldehyde though, and it is mostly just for educational purposes.

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[sethamederat]

nigel: has an entire labfull of fancy chem equipment
also nigel: doesnt have a fucking *spoon*

[jeffbrownstain]

"Oh yeah, I didn't have a spoon lying around anywhere, but I totally have broken plungers for days."

[kshitijnanda]

I wanted thank you, your videos have really helped me in my practical exams.

[clarsach]

I've always found it interesting that you can make minor modifications to aromatic, fragrant compounds and completely change their aroma such as is done more interesting is the way that isomerism and particularly chirality can make huge changes as with chiral isomers of carvone which can either smell like spearmint or caraway depending on their L or D form.

[MaxRay]

That 5 liter beaker made me laugh at the size of it when you picked it up. Didn't look that big in other shots and I wasn't thinking it would be that big

[LeonardGreenpaw]

I recommend a survivalist series, an apocalypse simulation where you get useful chemicals from common goods we can find while scavenging houses.
TEACH US HOW TO DEFEND AGAINST THE ZOMBIES!

[Metallikite]

-What a tedious synthesis! :D Extractions are my favorite workup procedure, though.
Well done as always! And I admire how you explicitly covered the mechanism.

[bradforddrake]

Injecting steam from an independent source would be best.Acetaldehyde will boil away and benzaldehyde is far more steam volatile than cinnamaldehyde.You also could reflux for 5-6 hours and keep the condenser water at 30Celsius(not the usual ice cold water) as acetaldehyde boils around 20C and will exit out of the condenser top! LeChatlier idea is by removing acetaldehyde you drive the reverse aldol reaction to make more benzaldehyde!

[sciencoking]

You said your beaker was 5 liters, but the sheer scale of that only became clear to me at 8:30. That is one massive beaker!

[tangentfox]

It's been a long time since I watched an old NileRed video.
"I didn't use organic solvents to be environmentally friendly." from the man who makes his FAVORITE CARCINOGEN.

[programablenuance]

Me coming to relax for a bit while studying for the MCAT just to see the retro-aldol reaction again

[kjpmi]

I don't know if you intend to be as humorous as you are but you have me cracking up through most of your videos. You have that kind of dry kind of witty humor that probably goes unnoticed by some people.

I'm curious, what is the blue bottle experiment?
And I would love to see a Q&A video, caffeine total synth, trimethylamine, and cyclohexanone oxime. So, I put my vote in for those next.

[newgrounds]

ooh, that smooth 60fps footage. Patreon money well spent?

[TheBladeOfTheHero]

Do you think you'd be able to make Formaldehyde, or is that too dangerous to try?

[plante]

You could make benzaldehyde by toluene oxidation, or chlorination/hydrolysis. it gives the useful benzyl alcohol as a side product and some trichlorbenzene, which can be used for dehydration of compounds or be turned into benzoic acid to use as benzene precursor.

Essentially turning toluene into 3 useful, less common chems in the lab

[Wishbone]

This gave me flashbacks to a chemistry class some 30 years ago. We were tasked with producing benzoic acid, and were divided into 6 lab groups. I don't recall what chemical was the starting point, but I do remember that the reaction involved boiling a solution, and that the chemical transitioned through benzaldehyde on its way to benzoic acid. So we were in a fairly small chemistry lab with six flasks of boiling benzaldehyde (almond essence), and well, let's just say the air got a little... dense. I don't think any of us craved marzipan for a while after that 😀

[jayzona]

Nile, you should do a lab/setup tour, that would be really neat

[dimaminiailo]

I think using a Dean-Stark trap for steam distillation is a better idea than distilling four liters of water. Why didn't you use distilled water from the receiver to replenish the level in the flask?

[Silentspeaker]

Could you have used DCM to remove the fine suspension of oil from the distillate, somewhat like you did in another video?

[JustinKoenigSilica]

reflux is just distillation without boiling something away?
so, in essence, just the phase change from liquid-gas back to liquid produces the Benzaldehyde?