It did more of such tests myself, using various kind of solid catalysts… The pathway seems clearly CBD to d9 and then d9 to d8 (with an intermediate at each steps). In parallel, depending on conditions, other minor products can be formed. A series of byproduct forms systematically. If oxygen is present, a bit of CBN and little amount of few other additional compound form as well.
If my attribution of d10 is right (close to cbc position, as I observed in rare cbd flowers, and more often in specific distilates), then there is not any of this forming in such synthesis experiments.
I tried similar tests on CBG, but got a series of two main unknowns in that case…
What analysis method are you referring to ? Retention times widely vary with method, column etc…
I guess this other main mysterious peak you see is the intermediate between d9 and d8, which might be the 8-OH-iso-HHC ( edited, not iso-d8-THC,) often referred to in some papers. Then, I also guess that intermediate between CBD and d9 may actually be 9α-OH-HHC (edited, not iso-d9-THC) .
Most synthesis attempt should thus results in binary or ternary mixture involving this 5 players (CBD, 9-OH HHC, d9-THC, 8-OH-iso -HHC, d8*THC) here, along with at least 10 minor compounds (including CBN, and the varin analogues of those 5 main components).
It also seems the varin analogues are more diffucult to transform, and that depending on condition, a portion of the main cannabinoid is driven to the varin line. Which at part explained the decrease in final expected yield.
Would you mind linking that literature, I can’t seem to find it online. I’m not sure why you’d get iso-d8 THC or iso-d9 THC. The stereochemistry at the 6a and 10a carbons shouldn’t be effected when converting CBD to THC
I haven’t been looking into proper modeling of the underlying process. I’m just maiking some empiric conclusion based on analytics, and what I see in paper, e.g. here or in this book.
I correct myself, that first intermediate between CBD and D9 would rather be 9α-OH-HHC and then the one between D9 and D8 would be 8-OH-iso-HHC. Thus, these are hexahydrocannabinols, and not tetrahydrocannabinols.
found another isomerization that goes strictly to delta 9
Example 3
Preparation of Trans-delta-9-THC
The cannabidiol from Example 2 (18.5 g, 58.8 mmol) was dissolved in dichloromethane (324 mL, 17.5 vol) and heated to 25° C. Triisobutylaluminum (5.9 mL of 1 M solution in hexane, 10 mol % catalyst) was then added via syringe and the reaction stirred at 20-25° C. for approx 20 h. After this time, HPLC analysis of the reaction mixture showed consumption of the cannabidiol and 94.8% trans-delta-9-THC. The reaction was quenched with water (1.6 mL, 15 equiv. based on moles of catalyst) and stirred for 1 h. After filtration through celite, the solvent was switched to toluene and the reaction mixture azeotroped to remove any remaining water. The solution of product in toluene (total volume ca. 92 mL) was used directly in the subsequent step.
I would be using TriIsopropyl Aluminium instead of the isobutyl.
from what ScienceSquirrel states its quite tame to use.
I have made triisopropylaluminium and it is not pyrophoric or particularly air sensitive. It does react with water but not in a spectacular way. (I think he is talking about the triisopropyl aluminium and not the isopropoxide that the thread might make one think he is talking about. he is prity much on the ball with most of this posts)
Did you really have to post about the organometallic catalysts? Most of us on here that are familiar with them have been purposely avoiding mentioning them in posts. How would you feel about taking those posts down?
In time I intend to put up every single journal and patent procedure for everything to do with cannabis chem
that I can.
I can understand your view.
though I do trust the admins over a sciencemadness and if one of them says they have made
isopropyl aluminium and not found it pyrophoric I believe them.
due to this alone that post has shown you something.
I dont tell you what to cook.
I would recommend though as you have a great knowllage of chemistry to put a comment as you have
about the danger of such a procedure.
I tend to agree
but it would be nice to have everything here in a nice thread by thread basis.
Yeah that’s not new info about isopropyl aluminium. I haven’t told you what to cook, if you want to use organometallic catalysts that’s fine with me. I wouldn’t recommend sharing the parents that can blow up the average ‘cook’ during this time period when a single lab explosion due to a cyclization/isomerization could lead to serious federal legislation that blocks cannabis processors from legally pursuing those ends.
do you honestly think that anyone is going to try and make a alkyl aluminium reagent to do a home
isomerization when any acid even the ones in the supermarket will do.
im not interested in using organometalics for isomerization.
I am interested in learning more about cannabiniod chemistry and what I find I would like to share.
If I get a general vote to stop I shall.
for now its one to the yes’s and one to the no’s
on second thoughts how are they going to get the sodium metal unless they are following nurd rages
work.
then if they are doing that and there making dioxane to purify the sodium and there making alkyl halides I think that you will find that isopropyl aluminium is not going to cause them trouble.
there was a reason I put my thoughts in the post and didn’t just say go for gold with the butyl compound.
though I am not sure that it is any worse than the isopropyl.
He did basically mention “this is dangerous as hell and do not attempt if you don’t know wtf you’re doing“. He provided a lead. Anyone doing this for commercial purposes can hire a trained chemist to train them how to conduct this procedure safely. Anyone who blows themselves up attempting this on their own without doing their research or getting professional assistance, well, they’re out of the gene pool. So it sounds like a win for the species.
No I don’t think an untrained chemist will synthesize their own organometallic catalysts. Any one working in a permitted lab that is zoned commercial can purchase these catalysts though. I don’t think warning people against using pyrophoric catalysts is enough of a safe guard. I worry that some amateur who has experience running a SPD or a closed loop will order a pyrophoric catalyst and attempt to use it after convincing themselves that they’re experienced enough to do so safely.
People blowing themselves up is not a win for the gene pool. That’s a tragedy… Explosions often times have collateral damage too. Is it a win for the gene pool when people not responsible for the fire or explosion get caught in its path? Seriously coppertop take an ethics class or something, whatever you need to do to not cheer when people lose their lives.
Freedom of information is one of our greatest privileges
And yes there are reactions that are dangerous but I can personally confirm that several isomerizations where the lead where papers , have now been developed with far safer/cleaner reagents and solvents by the industry
If freedom of information was a relevant concept I would happily affirm your point of view and discuss how wonderful it is to freely trade information for the purposes of education, innovation, and self growth.
In this case, however, the information or one’s freedom to access it is not at risk. I doubt anyone would be happy with these patents being censored by a government. I wouldn’t like that, that’s for sure.
I would love it if members of this community recognized that one fatal mistake on the part of a ‘cook’ like squig leads invariably to big pharma being the only industrial sector allowed by law to conduct cyclizations legally. I don’t care for ‘cooks’ just out of highschool to be advising other untrained, uneducated, profiteers in the ways of organic chemistry when lives are at stake. Shit take out the life or death element and the future of this industry is still at stake.
I hate to be the devil’s advocate here because we have plenty of them on this site already, but sometimes brining things like this into the light of discussion will make them safer. As @anon32743824 says, this information is already available. So is information on how you can easily blow your ass up with pyrophoric compounds, but unfortunately they are rarely in the same place. With the current status of the industry and processing labs/technology, I feel that it is currently a greater risk that an unknowledgeable operator would discover a dangerous method that they would try without understanding the dangers than that someone knowing the dangers of an operation (because I feel we expel much more emphasis on safety than your average ACS publication) that they see on F4.2k would try that procedure without taking the precautions necessary.
This is not to say that amateur chemists don’t often take the danger of their endeavors too lightly, just to say there is an expected value calculation to be made here. Also worth noting, we as an industry generally care more about patients/customers being unknowingly subject to harm than lab operators killing themselves by accident and there are plenty of half-assed procedures that will poison the shit out of grandma floating around that haven’t been censured. Our goal should be to educate as much as possible to make patients and operators safer, but the patients always come first IMO.
I wish I had a strong rebuttal to that, but I don’t. There’s a lot of merit in aggregating these risky teks in the same place that safe lab construction and safe reagent handling practices are discussed.
It doesn’t alleviate any of my concerns though. 18 months ago I was the only person in my social circle that had read any of these patents. That was frustrating because I had no one to discuss this stuff with that took it seriously. By the time isolate dropped to $1,200 per kilo just about every processor I know had begun to discuss the potential profit margins involved in cyclizing to yield thc. Today, with isolate prices around $500 per kilo, even growers that I know with very limited extraction experience are talking about cyclizing with dollar signs in their eyes. I’d prefer if the least educated among us didn’t have instantaneous access to a patent that promises them a 99.99% conversion to D9. Maybe it’s different in other parts of the world, but here in Flint, Michigan I can guarantee that someone is going to try to escape poverty by synthesizing thc… And there will be explosions and lab fires. That doesn’t thrill me.
Actually the difference is that they have to pay. That’s a huge threshold to cross for most poor people. I believe that it’s the poorest people who would be the most interested in producing thc for pennies on the dollar when compared to extraction. Also, a major difference is that there are no members on here selling unsafe SOPs involving triisobutylaluminium. Whereas now there is mention of it on this site. The differences are pretty obvious imo.
