> chemistry > reducing-agents > reduction-of-vanillin-to-vanillyl-alcohol-by-bh4-rhodanide

Late Night Chemistry: Vanillyl Alcohol

Rhodanide - 2020-03-08

Late Night Chemistry is back with a second episode! Today, I show you the synthesis of Vanillyl Alcohol via the reduction of Vanillin with Sodium Borohydride. 



I'm not responsible for damage to persons or property caused by the replication of this experiment. 

Consider supporting me! https://www.patreon.com/Rhodanide 

My Twitter: https://twitter.com/Rhodanide



Songs used:


Mr. Fletch - Flare
Mark Shreeve - High depths b freedom

Random Experiments Int. - Experiments and syntheses - 2020-04-08

Nice synthesis! I can't believe it took me so long to simply have a look at your channel..... These videos are great! I like the music and the VHS look. Of course you've got a new sub!

Rhodanide - 2020-04-08

Thanks REI, that really means a lot! Seems everyone has a bit more free time to look around these days.

Benjamin Bradshaw - 2021-04-18

Love the visual chemical equation! I forgot about the methoxy group and I was picturing a dihydroxyphenyl ethanol for a minute there because of the molecular formula so that came in handy for me

Benjamin Bradshaw - 2021-04-18

thought of that as the product and the corresponding aldehyde as vanillin

ReactiveChem - 2020-03-08

That time lapse of the crystals crystallizing was beautiful

Rhodanide - 2020-03-10

I agree! Glad I caught it!

Tim Mulm ll - 2021-07-18

How different is the smell of Vanillyl alcohol compared to the educt, Vanillin respectively?

Ariadna - 2020-03-08

I loved when you whent outside to take some snow hahaha also very pretty crystallization point of view

Rhodanide - 2020-03-08

Yeah, gotta go further out in the yard now for snow now that it's warmer. I also enjoyed the crystallization!

Riccardo Grigolato - 2020-03-08

very nice, first time seeing a reduction with borohydride thx

Rhodanide - 2020-03-08

Organic, you mean? I did an inorganic Borohydride reduction of Cobalt in the last LNC episode. Thanks for the kind words!

Stanford - 2020-03-10

Can you show how to make corrosion resistant electrodes

Definetly not a Comment - 2020-03-08

Nice bit of variation from the usual content.

Rhodanide - 2020-03-08

Little bit of o chem won't hurt :)

PoorMansChemist - 2020-03-08

Very cool man! Those are some nice looking crystals. :-)

Rhodanide - 2020-03-08

Thanks! They also smell very nice as well.

PoorMansChemist - 2020-03-08

@Rhodanide I'll bet they smell WONDERFUL! I should really give that a try sometime...

Full Modern Alchemist - 2020-12-09

I had that exact scale for a while and it did shit like that to me all the time. It finally died a few months ago.

Tomas Frankovich - 2020-03-08

Some organic this time! Sweet!

Rhodanide - 2020-03-08

Hah, sweet... y'know, cause Vanillin...


..yeah I'll see myself out.

Tomas Frankovich - 2020-03-08

@Rhodanide haha! Some more organic stuff would be really cool though, maybe try some BODIPYs or something!

Daniel Cezar - 2020-03-08

THank you so very much

Rhodanide - 2020-03-08

You're welcome! Thank you !

ZodaChem - 2020-03-10

My advice is to make also vanillic acid and esterifies it with vanillyl alcohol to make vanillyl vanillate.

Rhodanide - 2020-03-10

That's a thing?!

ZodaChem - 2020-03-10

@Rhodanide What you mean ?

Rhodanide - 2020-03-10

@ZodaChem didn't know Vanillyl Vanillate was a thing.

ZodaChem - 2020-03-10

@Rhodanide do you think is not possible to synthesize ?

Rhodanide - 2020-03-10

@ZodaChem I have no idea

Davide Aezakmi - 2020-03-08

Why does the HCl produce hydrogen? Does the vanillyl alcohol oxidize again?

Rhodanide - 2020-03-08

If I had to guess it's from residual Borohydride.

sjoerd klomp - 2021-01-02

I think it's because the Borohydride produces hydrogen when reacting with water. Like so: BH3 + 3H2O --> B(OH)3 +3H2

xerolad - 2020-03-08

Very nice!

Rhodanide - 2020-03-08

Thanks!

xerolad - 2020-03-09

@Rhodanide Using snow as an ice bath amuses me lol (I'm originally from Ontario)

Scarecrow Airsoft - 2020-03-30

Hey man check your message requests made a new Facebook got the pistol for you

P EDUARD CHRISTIAN - 2020-03-08

Where did you get nabh4

Rhodanide - 2020-03-08

Online.