Turning vanillin into piperonal but not for drugs | Part 1 (3,4-dihydroxybenzaldehyde)
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- Опубликовано: 13 июл 2024
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Today we do a demethylation of vanillin to yield 3,4-dihydroxybenzaldehyde. Next video we will do a methylation of 3,4-dihydroxybenzaldehyde to yield piperonal. I swear it's not for drugs!! Thanks for watching!
Sources:
erowid.org/archive/rhodium/ch...
www.acs.org/molecule-of-the-w....
www.sigmaaldrich.com/US/en/pr...
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I have a lot of protocatechualdehyde along with rare compounds I can send you for example BBr3, Benzyl chloroformate, Boc Anhydride, halo ketones, amines and many more. I would love to see what you can do with it. Let me know if you are interested
Bro, can you do ricin from an issue of Breaking Bad?
I know this left field but could you make a series on reducing cholesterol into 19c derivatives. Just curious?😅
Lmao That Chemist becoming the police of chemtubers is a funny thought. Great to see you all poking fun :)
Wait until he actually starts creating practical chemistry content....
He probably doesn't realize how hard it is to do a reaction outside of a real lab, (in a shed on Australia, lol.)
Having all the reagents you need at your university's disposal is much different than going to a hardware store to source everything, and do it in an garage or shed.
(I'm assuming he isn't an amateur chemist).
@@Ryan-lc4blI mean, no one asked anybody to do chemistry on their own garage. If you can’t make proper analysis then don’t claim you synthesized your product at all, it is that simple. Yes amateur chemistry can be fun and with proper safety equipment and education I encourage people to train and challenge themselves. But chemistry is an actual science, you can’t juste randomly claim what you want to. Otherwise that’s just not chemistry. Also, if making a TLC and melting point check is actually THAT hard for you, it’s probably a bad idea to make some amateur « chemistry » content for your own safety. Ofc no one has a personal NMR at their disposal, but come on, very basic analysis could still be done and discuss about the lack of analysis is literally : free.
@@Tom-to7dy
I know that one must prove whatever product you got is actually there in order to claim you have made it.
But that doesn't mean that just because you can't prove it, it's not in there are all (I know that sounds against the scientific method, but if your reaction products are easily separated, or there're few byproducts, most amateur chemists don't bother with testing their product for purity, because usually others have already performed the reaction many times and the results are quite predictable (alright, everyone's reaction products will be slightly different in composition).
I know that melting point analysis is quite easy for an amateur chemist, but most amateur chemists don't do long multi-step organic synthesis anyways (with few exceptions).
Anyways, I'm not at all against doing analysis of your products, but we must be realistic, amateur chemists that are just performing simple organic synthesis generally don't test the product not because they're against the scientific method, or just lazy, just not necessary for ALL reactions (even distilling your product can give some information on the purity - i.e. azeotropes).
My favourite part is you feeling if it is exothermic by hand, rather than using the temperature measuring stick that is inside
I low-key sometimes just stick my finger in and give it a bit of a taste my cooking always 🤤 😋🤤🤤🤤🤤🤤😋😋😋😋😋
every organic chemist, ever
The temperature stick isn't as accurate as hands.
Better yet, use your tongue as a thermometer. :D :D
I enjoy video creators who communicate through the camera, not to the camera.
Both are cool but I also prefer it this way
@@iuristasiv9360 I compliment you for an amazing creation sir, keep finding cool stuff to do.
@@xbhendrix what creation my friend? You're talking about my videos?
@@xbhendrix thanks btw!
yes sir, your ability to record your processes and still perform your task at a high level is an admirable accomplishment. make it look easy, when in reality, nothing is easy. @@iuristasiv9360
Wow that was a really cool reaction! We appreciate you so much. Also absolutely love the merch. Going to scoop me up a hoodie and that bucket hat right now!!
The editing, the camera quality, the lighting,...everything has been upgraded. even there are less lame jokes now. just straight up chef kiss content. its giving professional.
you really steped up your game. congrats on the sponsors. you really invest money in your videos. you deserve big success.
Thank you for saying that :)
@@chemdelic- Keep the great humor going, it's best part of yellow chemistry. ;D ;D
Potential imputities are pyridine hydrochloride, vanillin, 3,4 dihydroxybenzoic acid and aldol condensation products. I would not expent much of the pyridine since it should have stayed in the water layer. You probably could have gotten less impurities by a salt wash and then sodium carbonate wash of the ether before evaporating. The aldol condensation products are probably the major impurity and not avoidable. A tlc plate could give you some idea of the distribution of the impurities.
honestly even a 52% yield is pretty decent for that reaction
Idk how the erowid source got 87%. Unfortunately it’s even less due to the impurities:(
If you can't trust Erowid, who can you trust?
@@chemdelicSeemingly small things like @1:45 when you mention not drying the DCM compound to have huge impacts later on.
I'm not saying that is the smoking gun in this experiment, just using that step illustratively. I really appreciate your completeness especially regarding yields and hypotheticals outlining your analytical process. Great work.
It has inspired me to review the Erowid lit workup. I'm sure someone else will beat me to it but I'll follow up if I find anything glaring.
Home organic chemistry without TLC is like traversing a forest in a moon-less night.
I have TLC, but didn’t have a pure product to compare to. I actually just received it today so I could do one now :)
@@chemdelic you can do TLC even without pure standard, you can guess the product from the biggest spot and also from a different Rf in comparison to the starting material.
TLC is very common for monitoring undergoing reactions where you have just the starting material to compare it to.
🤣 “I don’t want That Chemist to make a video about me” that’s fucking hilarious
Hi. I haven't done chemistry but I am very familiar with reaction you are doing. Some notes. Demethylation reactions are sensitive to water so using non dry DCM reduced your yields. Second and more important note is that demethylating vanillin is very very very hard and your yields are about right where I expected them to be. If you would to find a method to demethylate vanillin with over 90% yields you would be rich.
I heard ethyl vanillin is easier!!
@@chemdelic I am not that familiar with ether cleavage so I cant comment on that. What you can also do is to search for demethylation in google schoolar. There are new methods published since writeups in erowid. Maybe you will find something you like more.
“Wutcha doin?”
“Watching a chemistry video.”
“Oh cool what about?”
“…not drugs.”
please continue with this series :c great content!
I really like your videos dude. Very interesting reactions. I've always been very interested in pharmaceuticals and extracts like nutmeg and vanillin and saffrol
I can't get enough of your content
Good stuff Chemdelic. You know you can achieve the same using pyridine*HCl and a microwave? Just gas some pyridine with dry HCl gas, mix with vanillin, nuke in microwave, and you get protocatechualdehyde. In the next step, don't forget to include phase transfer catalyst like fabric softener.
One day the DEA will text both of us back don't worry 😊 nice video as always the editing quality is always improving
the intro is so over the top i love it lmfao
The white solid is presumably pyridinium chloride, the result of pyridine coming into contact with the generated hydrogen chloride gas. 😊
Interesting! Thanks for sharing that
Can confirm
White fluffy stuff coming out of dcm is py.HCl 99% of the time 👍👍
Yup that's what the paradine is for.❤
Your videos are getting better and more entertaining and after reading a bit of claydens organic chemistry i finally start to even understand what youre doing XD
That’s awesome brother!!!
That segue was brilliant.
Found your channel just yesterday and I want to say that you are absolutely mad lad, which highly inspires me. You know, I'm a huge psychonaut forums enjoer and there have long been rumors about the extraction of psilocybin crystals. Since you have dea as your best friends and got that Shulgin spirit whispering into your ears what you think about the extraction of these extraterrestrial guys?? I tried to do it myself and even got the crystals, but they didn't work at all:(
Great vid! I would've loved if you explained the mechanism tho
You're absolutely on a watchlist
Wait until people who think he doesn’t know that latch on.
Then they’ll be on a different watchlist.
The stupid one.
I say the stupid one because everyone knows there is the smart one and the stupid one.
I havent watched the chemistry part yet, but the intro already man. You're the fucking best (together with chemiolis IMO)
A good, old-fashioned setup for melting point is to use a thiele tube and a capillary. Both can be bought for cheap nowadays
Now every chem channel is afraid of getting into a @That_Chemist video and making at least melting point test, while saving for a 300MHz NMR 😃
An interesting video and everyone loves yellow chemistry!
pyridine and vanillin accord. that is quite some aroma to spray all over the lab. great vid..
Ah sweet, more mystery compound!
Definitely do another crystallization.
Cool vid again ✌🏻👍🏻
Thank you!!
I’m wondering if you can perform a ketalization using your product and formaldehyde with some p-toluenesulfonic acid to form piperonal, or if it would just react with itself in those conditions
ah, I remember chemplayer trying this back in the day. brings back memories :')
Get one of those old school melting point apparatuses like a thiele tube and some capillaries closed from one end. tiny bit of compound at the bottom of the capillary, strap the capillary on your thermometer and heat in thiele tube
Great video. Only criticism is i wish youd show the reactions taking place on screen.
You might be able to push a bit more dihydroxybenzaldehyde out of your acidic aqueous phase by chucking in a tonne of ammonium chloride and reextracting with ether. Or it might make it worse. Or ethyl acetate is probably a better extraction solvent.
You're so good with chemicals!😣😩
Lmao the intro is hilarious😂
Can probably use AlI3 as the Lewis acid, right? Can generate it in situ from alu foil and iodine. Although you might need a different hydrogen transfer catalyst with this. DMSO in the paper I'm going to use for ether cleavage. Also less annoying to get for hobby chemists than pyridine.
I probably would have just gone with sulfuric acid instead of pyridine to complete the deacetylation, but is an interesting bit. just hitting that like button....
Thanks
Thank you so much brother :)
Very beautiful young alchemist!
I'm waiting on you to come up with the chemical makeup of CBR aka 2-gb
I promise to not use the information in this video to access the gateways of boundless love
Great job and good luck!
Chemdelic, do you have any reccs for learning chem/organic chem outside of schooling? It's always interested me, though the schooling model of just testing rote memorization always put me off from introductory courses back in school/college. Can't afford another 'education' anyways nor would I want one. Unsure how comprehensive Brilliant is & if it also teaches the application of chemistry rather than just theory.
You can buy textbooks on organic chemistry pretty cheap online (I like Clayden’s), and many schools have put their organic chemistry classes on RUclips for free :)
Do they use this in mdma?
Have you started working on step II? When do you think the next video will be finished I like your work u really stepped it up congrats.
I’m waiting on some reagents! But hopefully will be done soon
Awsome thank you for replying, you rock!
Neat!
You should make a Can you trust That Chemist video that just says I dunno probably
Very nice! I wonder how effective hot sulfuric acid would be at performing an ether cleavage on vanillin. From my experience, it works really well with ethylvanillin, which gave me close to 70% yield...and let's be honest, literally anything is better than having to deal with the stench of pyridine, haha!
I need to try that. This one from my “source” (Erowid) said they got 87% yield. I call cap🧢😂
@@chemdelicJust make drugs already stop pussyfooting
Maybe you should have washed your aquise layer a few times with ether. That should help with the Vanilin impuritys
Yeah maybe doing an ether wash before I add HCl would help.
I like the disclaimer voiceover🤣
Is it possible to make methylene blue?
2:12 Aluminum chloride doesn’t produce HCl, however it I still very acidic and fumes vigorously in air.
Can you make piperonal from ethyl vannilin Its more OTC
Cool!
it is definitely not for drugs mr cop
I think you had to try a crystallization and some colorimetric test.
Hehe the funny chemical
This might a stupid question but isn't extremely risky to record and post yourself making controlled substances even if the end result isn't something bad or illegal or what ever
It isn’t controlled at all :)
What is that molecular seive or seed btw thanks for the video.
3A molecular sieves
i cant wait until you make a patreon so i can finally learn how to make MDMA
I have a Patreon. Link in description!
Part 2! 😅
Iso-vanillan can be used as a precursor to synthetic morphine per the Gates synthesis i think
Yeah - and I believe he used Pyridinium Chloride to demethylate the codeine and yield morphine. That was back in 1953, I think. Nowadays, Boron Tribromide would be the demethylating agent of choice, IIRC. At 71, my memory isn't quite what it used to be, but I believe that refluxing in concentrated HBr works to cleave some aromatic methoxy groups, like as in oxycodone to oxymorphone.
Are you sure you did not use Ethylvanillin instead of Vanillin? Just asking.
This might very well be the best way to get to Piperonal.
Great upload.
Thank you.
Greetings,
Jeff
I used regular vanillin but I have been told that ethyl is easier
@@chemdelic Im not qualified to check on it while i did not study organic chemistry, but is the synthesis exactly the same?
Greetings,
Jeff
Anhydrous Aluminum trichloride... my oh my what a lovely chemical. Where can I get some at?
SynthetikaChemicals!! Use promo code “Chemdelic” and you can get 10% off too :)
I dont get how it went from the aquaous into the organic layer. You didnt change anything like reacting it with NaOH. Why was it in the aquous layer, then in the organic? You put HCl BEFORE the seperating step.
The HCl was to push it into the aqueous layer!
3:06 Bro what 😮
Drug enforcement hates this synthesis!
Whats next? Catechol (made from Salicylic acid) to 1,3 benzodioxole???? You will surely be DEA's favorite person by the end of this year.
the damn yellow chemistry
The clash Royale meme was pure gold 😂
"Get-there-itis" applies to chemistry as much as aviation.
2 part.. 3,4 dihydroxybenzaldehyde / piperonal ? 👌😬
Cool
"Don't worry, I'll show you exactly why it's so important"
Uh oh
Demon core (for fun) tutorial when?
I cant wait to do this myself, in minecraft
piperanal
not a single recryst? Seriously dude thats the basic procedure for simple purification specially if you have the blessing of having a crystalline/solid product. You had a diffferent m.p than literature, so recryst and test again until it matches or gets the closest possible. That is basic
Very basic.
It's really not needed in this case since the m.p. is very close to the literature range and the compound will soon be used in the next reaction. It's good he even measured m.p. since a lot of chem youtubers don't even bother with that.
Merch linki?
Oh yeah I forgot to add that lol
We all need a little more spice in our life.
MMMMMMmmmmm. Vanilla-flavored rotten fish! Wokka! Wokka!
that impurities duality statement made me dizzy 😅
Why would these compounds be of interest to the dei dea
As long as it's consensual
suuuuure.
This gangsta using AlCl3 in a rain storm...outside. Reminds me of my very first grignard in orgo 201 which failed cause it was raining out and our hoods didn't have nitrogen blankets.
I was compelled to give the video a thumbs up immediately upon reading the title.😂 But c'mon couldn't you have drawn your own reactions instead of stealing from Rhodium!!!
Yes I could have, but I didn’t have a lot of time for this video due to school and other commitments. I would have hand drawn and gone over mechanism if I had time :)
@@chemdelicapparently you did not had Time either to find your own project ideas, theif
next video, meth please
69 views. Nice
all the chemists here gave the 🤨 face seeing the product being made
Yellow chemistry 😔
Soyuz rocket lmao
I would love to make some 2C-I OR 2C-B . When it was legal i got my hands of a gram of pure 2ci and its still my all time favorite drugs. Better then heroin, MDMA. Mushrooms, acid, meth, crack, cocaine,ketamine, dmt or xanax. It makes you feel the same love and warmth that MDMA does but your tripping your ass off and have the psychedelic headspace. I can eat on it, sex is amazing, and it has zero come up or come down. You high as shit and then boom 5 hours later your sober. Man i miss it, its nearly impossible to find since it was made illegal. It never got popular like other RC drugs did. To bad
bruh
Do you know that stealing projects from others is not fair ? I know what you did to Creatybin
Hello. The "project" is based on well-documented pathways that Creatybin did not create. IF he made that specific pathway through his research and it was published by him specifically, then I would give credit to him. Also, anyone can make a video on it. So to say that I "stole" a project just by someone mentioning a pathway they were going to do is completely inaccurate and quite immature as a response. I have seen this pathway before and already planned on making another piperonal video. I would have done this with or without him saying he was going to do it. If he is going to say that I stole a pathway, he might as well contact everyone who also went through this pathway. Like cmon bro🤣🤣💀
@@chemdelicawesome
🤮 pyridine spills
The worst! Like 80ml too :(