CBD to CBN

Just going out on a limb here, as I’ve had some mental masturbation about a synthesis of CBN from CBD as a starting compound. I am aware of a synthesis from THC as a starting compound from the paper linked below. Could anyone give some insight on what steps could be taken, theoretically to produce CBN directly from CBD? My thoughts are maybe start by deprotonating the hydroxy group on CBD (either would work since that portion of the compound is meso) then perhaps a grignard reaction to remove the vinyl and close the ring, then di-methylate with DMS? Thoughts?

Structure of cannabidiol. VI. Isomerization of cannabidiol to Tetrahydrocannabinol, a physiologically active product. Conversion of cannabidiol to cannabinol
Adams, R., Pease, D.C., Cain, C.K., and Clark, J.H.
J. Am. Chem. Soc., 1940, 62 (9), pp 2402–2405
DOI: 10.1021/ja01866a040

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That paper you posted was pretty neat. Funny reading papers before the advent of computers. Anyways, Deportation of the hydroxyl with a big bulky base (e.g. Pyridine) is fast and has a 1,5 bond path. So I think the ring closure is intramolecular (formal negative charge on the oxygen and a quasi positive charge on the alkene) via some type of aldol rxn. Just my thoughts.

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Here is a paper describing a one step reaction of CBD and THC to CBN with molecular iodine. They report yields of 72% using a 2 molar equivalent of sublimated iodine refluxed in toluene for an hour.

https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00946

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Yup That will work. Thanks

Thanks! That’s exactly what I was looking for

I grew up before the advent of computers. What a difference in how people go about their daily routines now. Still though I remember sitting in philosophy class debating about what computer tech would some day bring us.

Not one single person in that class postulated that it would be used for wide spread dissemination of pornography or that the preferred method of interacting via computers would be something that earned names like “troll”, “flaming”, or any such other sort of use like this. We mostly speculated that computers would set folks free from tedious tasks and that folks could then focus more on positive intellectual pursuits and a freeing of the mind for higher intellectual thoughts.

Then along came a company named Apple… now there is a computer in front of nearly every face 24/7 and life seems all the more tedious now and void of what we saw as a freeing of the mind. Instead of freeing the minds it seems to enslave them as an addiction and we never saw that coming.

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Chear up thx to computers i have been able to get a Tiny bit of your knowlidge
But Yes i agree great tool for info but not for 24/7
Hope You read this feeling strong and good hang in there :facepunch:

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Lol when I get stoned I get philosophical. It does make me wonder some times how the world changes so fast. Your point is well taken and well timed. That post WAS a downer lolz and my mistake and apologies.

Without the use of the internet as my only means to education I could not learn what I needed to refine. I owe everything regarding refinement to this easy access to good knowledge. This forum is a great example of the good. Not only have I gained knowledge but even some of the legends of cannabis have stopped by to meet me in person. Sure, they usually run screaming from the house but… I gotta be me lol.

Chalk up my post to a bitter old man who needed a good BM and got philisophical. The world just seems to have gone to hell when they stopped making chariots. I am beginning to think nobody even knows how to make a even a wheel for one anymore. Now it is all these damn horseless carriages and a whole generation of kids who don’t even know how to field dress a deer OR an enemy of Rome…Plus now there is the sliced bread tech too… yep, the world is changing… :stuck_out_tongue_winking_eye:

Just be patient with me. I can learn. Now… let’s talk about the “undo” button that pops up under my thumb on my iPad… who’s glorious idea was that one???

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Would you be using a dean stark trap for this.

Maybe I am misunderstanding the question, but they just use a condenser on top of their boiling flask. You could use that trap if you wanted to collect the water from your extract while your reaction was running?

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Does anyone have the full text of this paper?

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also future reference @rushfarm just paste the link to the abstract into sci-hub.tw works most of the time

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Search bar it s been posted by several members Maybe one is complete
There is a beter method in th glg
Sop division by @anon93688

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In the glg sop where does the 30% peroxide come into play?

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No where that i know of it is based on a sulfur reaction

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Hmmm. Wonder why its listed as a component of the list of needed materials?

The hydrogen peroxide is meant to neutralize the hydrogen sulfide

Do not put that shit on dry ice like the SOP says or you’ll freeze the trap and it’ll stop working

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Is that after the sulfide reaction is done and cbn crude is prepared?

No this is used during the reflux

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Interesting. The sop doesnt discuss or put that step in at all. What ratio of peroxide to total solution of cbd/sulphur?