understand completely it happens all the time. I have to keep a notebook of things I want to search because ill think about walk to the computer... pull up the search page and draw a blank.... I find adderall stops this 100%
Sedit
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- Foundress Queen
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2bfrank
- Guest
Thats interesting, I definately need to get a handle on my stress when it comes to exams Im telling you, Stess in general, but exams and hi pressue stuff big time. Talk to you later
drone1240
- Subordinate Wasp
- Posts: 105
Can MeOH be used for THC extraction or is it to toxic. Also after super-critical butane extraction is there still THC in the feed stock or is it all gone.
NeilPatrickHarris
- Dominant Queen
- Posts: 274
Can MeOH be used for THC extraction or is it to toxic. Also after super-critical butane extraction is there still THC in the feed stock or is it all gone.
MeOH is used as a crude extraction solvent or recrystalliztion solvent by many, you just need to be sure to remove all the MeOH before consumption. yes it's very toxic.
drone1240
- Subordinate Wasp
- Posts: 105
Thank you Neil. Yesterday in oz I saw a groovy little bar that looked like a green chocolate bar. I have been looking on erowid and the lyceum for ways to morph stock into those delectable little treats. I am under the assumption that the bud and water leaves are pulverized and than ground into dust. This is then pressed into blocks. Does solvent need to used to wet stock before pressing cake? I will keep UTSE but a little guidance would be appreciated.
Happyman
- Subordinate Wasp
- Posts: 122
So I got two thoughts on my mind. One is very specific extraction methods. I would like to know more about them so suggestions on articles I could read. Getting 5-methoxytryptamine out of nutritional products. It sounds like an impossible task to me. Second is some articles on steric hindrance which I know little to nothing about. Also how steric hindrance relates to solvents. Thanks.
heisenberg
- Dominant Queen
- Posts: 268
@happyman
An acid base extraction would do it, followed by recrystallization. Naphtha would probably work to extract the freebase, but I dunno what would work best for recrystallization.
An acid base extraction would do it, followed by recrystallization. Naphtha would probably work to extract the freebase, but I dunno what would work best for recrystallization.
Vesp
- Administrator
- Foundress Queen
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Other issues might arise if there are other compounds that will act similar in the product as well. Is that the issue you are having?
Happyman
- Subordinate Wasp
- Posts: 122
Well I wrote a two page post about my concerns then I found that our old friends at zoklet finally came up with something useful (http://www.zoklet.net/bbs/showthread.php?t=81798). So my interest in extraction has faded, but thanks for the help! Steric hindrance is still a big for me.
heisenberg
- Dominant Queen
- Posts: 268
Steric hindrance is still a big for me.
Steric hindrance is an issue of reactivity, not extract-ability. Could you be more specific with your steric question?
Happyman
- Subordinate Wasp
- Posts: 122
Why does dimethyl sulfoxide or tetramethylene sulfone support dialkylation while more "simple" like ethanol do not?
Evilblaze
- Guest
Another question:
Benzodifuranyl compounds looks really nice, but it's hard to get the chemicals to prepare them. Or not so hard, but really nasty and bad to work with them (especially n-BuLi).
My idea would be to start the reaction from hydroquinone bis(2-hydroxyethyl) ether what is cheap as dirt and easily obtainable.
The original synthesis is to make 2,5 dibromo hydroquinone bis(2-bromoethyl) ether somehow (usually from hydroquinone and 1,2 dibromo ethane and a little bromination) and react this with n-buthyllithium to get the benzodifuranyl. The main goal would be to get rid of the n-BuLi from this synth.
There is an other method, what can be good... The Wurtz-Fittig Reaction. This reaction goes between aryl and alkyl halides with sodium. The big problem with this would be that, that the alkyl halides could also react with the alkyl halides (Wurtz reaction) in presence of sodium, so it can be a really big problem for me if the alkyl halides would react with just the alkyl halide chains and not with the aryl halides.
Any ideas? Or I just have to get some n-BuLi?
Benzodifuranyl compounds looks really nice, but it's hard to get the chemicals to prepare them. Or not so hard, but really nasty and bad to work with them (especially n-BuLi).
My idea would be to start the reaction from hydroquinone bis(2-hydroxyethyl) ether what is cheap as dirt and easily obtainable.
The original synthesis is to make 2,5 dibromo hydroquinone bis(2-bromoethyl) ether somehow (usually from hydroquinone and 1,2 dibromo ethane and a little bromination) and react this with n-buthyllithium to get the benzodifuranyl. The main goal would be to get rid of the n-BuLi from this synth.
There is an other method, what can be good... The Wurtz-Fittig Reaction. This reaction goes between aryl and alkyl halides with sodium. The big problem with this would be that, that the alkyl halides could also react with the alkyl halides (Wurtz reaction) in presence of sodium, so it can be a really big problem for me if the alkyl halides would react with just the alkyl halide chains and not with the aryl halides.
Any ideas? Or I just have to get some n-BuLi?
embezzler
- Subordinate Wasp
- Posts: 228
What reaction conditions do you propose for the first step in the scheme below? I would be worried that the hydriotic acid (and any HBr that is generated) could cleave the ether groups.
Evilblaze
- Guest
Quote
1,4-Dibromo-2-(2-bromoethoxy)-5-methoxybenzene
(9). Bromine (21.8 g, 0.137 mol) in CH2Cl2
(50 mL) was added dropwise to a mixture of
1-(2-Bromoethoxy)-4-methoxybenzene (14.9 g,
64.6 mmol) dissolved in CH2Cl2 (500 mL) with a catalytic
amount of Fe filings. The reaction continued for
24 h before the mixture was washed with 3 M NaOH,
3 M HCl, and brine. The organic phase was dried over
MgSO4 and the solvent was removed in vacuo to give
an orange solid that was recrystallized from EtOAc/hexanes
to yield 21.5 g (85.3%) of 9 as off-white crystals: mp
64–65 C.
Just instead of the 1-(2-Bromoethoxy)-4-methoxybenzene the 1,4-di(2-iodoethoxy)-benzene would be used.
The iodination... That's a risky part. Maybe I would prefer to use PI3. Not the red phosphorous + iodine method, the other one. White phosphorous and iodine in carbon disulfide (if I remember correctly, somewhere I have some of this). In this case, no HI would evolve from the reaction mixture and this why no problem would be caused.
Or just go by the original synthesis with the 1,2 dibromo ethane. It has lower yields, but everything is cheap for this part of the synt.:
Quote
1-(2-Bromoethoxy)-4-methoxybenzene
A solution of 4 methoxyphenol
(10.1 g, 81.3 mmol) dissolved in acetone
(100 mL) was added over a 12 h period to a mixture of
1,2-dibromoethane (35 mL, 0.41 mol), finely powdered
K2CO3 (35 g, 0.25 mol) and acetone (300 mL) at reflux.
The reaction was held at reflux for 125 h before the
K2CO3 was removed by filtration. After solvent removal
in vacuo, the remaining residue was combined with
CH2Cl2, washed with 2.5 M NaOH, 1 M HCl, and
brine, and dried over anhydrous MgSO4. Evaporation
of the volatiles in vacuo yielded an orange solid that
was treated with a 10% CH2Cl2–90% hexanes solution
(100 mL) to precipitate the dimeric material present.
Following filtration, the filtrate was evaporated in vacuo
and recrystallized from EtOAc/hexanes to yield 8.42 g
(44.8%) of 1-(2-Bromoethoxy)-4-methoxybenzene
as translucent sheet-like crystals (mp 50–
51 C)
But in this case I would get 1,4-di(2-bromoethoxy)-benzene instead of the 1,4-di(2-iodoethoxy)-benzene....
embezzler
- Subordinate Wasp
- Posts: 228
Well if the aim is to remove the butyl lithium to make it safer then I would definitely remove all thoughts of the white phosphorus since it is probably worse
1,4-Dibromo-2-(2-bromoethoxy)-5-methoxybenzene
(9). Bromine (21.8 g, 0.137 mol) in CH2Cl2
(50 mL) was added dropwise to a mixture of
1-(2-Bromoethoxy)-4-methoxybenzene (14.9 g,
64.6 mmol) dissolved in CH2Cl2 (500 mL) with a catalytic
amount of Fe filings. The reaction continued for
24 h before the mixture was washed with 3 M NaOH,
3 M HCl, and brine. The organic phase was dried over
MgSO4 and the solvent was removed in vacuo to give
an orange solid that was recrystallized from EtOAc/hexanes
to yield 21.5 g (85.3%) of 9 as off-white crystals: mp
64–65 C.
It seems a nice bromination reaction and 85% yield isn't half bad either however would using the 1,4,-di(2-iodoethoxy)-benzene not lead to displacement of the iodine on the alkyl chains by the bromine? or is your intention to use elemental iodine instead of bromine and remove all bromine molecules from the product? With two halogens I would expect a combination of halogenated products being formed which may mess with the final reaction.
For the original synthesis 125hrs is a long time to be watching a synthesis but as you said the reagents are easily obtainable and a reflux with acetone is unlikely to give difficulties. I don't much like the sound of the dimer in the work-up but it may not be that bad.
Since I am unfamiliar with the Wurtz-Fittig reaction and dislike my own ignorance here are two papers I am reading on the reaction mechanism that may be of interest.
1,4-Dibromo-2-(2-bromoethoxy)-5-methoxybenzene
(9). Bromine (21.8 g, 0.137 mol) in CH2Cl2
(50 mL) was added dropwise to a mixture of
1-(2-Bromoethoxy)-4-methoxybenzene (14.9 g,
64.6 mmol) dissolved in CH2Cl2 (500 mL) with a catalytic
amount of Fe filings. The reaction continued for
24 h before the mixture was washed with 3 M NaOH,
3 M HCl, and brine. The organic phase was dried over
MgSO4 and the solvent was removed in vacuo to give
an orange solid that was recrystallized from EtOAc/hexanes
to yield 21.5 g (85.3%) of 9 as off-white crystals: mp
64–65 C.
It seems a nice bromination reaction and 85% yield isn't half bad either however would using the 1,4,-di(2-iodoethoxy)-benzene not lead to displacement of the iodine on the alkyl chains by the bromine? or is your intention to use elemental iodine instead of bromine and remove all bromine molecules from the product? With two halogens I would expect a combination of halogenated products being formed which may mess with the final reaction.
For the original synthesis 125hrs is a long time to be watching a synthesis but as you said the reagents are easily obtainable and a reflux with acetone is unlikely to give difficulties. I don't much like the sound of the dimer in the work-up but it may not be that bad.
Since I am unfamiliar with the Wurtz-Fittig reaction and dislike my own ignorance here are two papers I am reading on the reaction mechanism that may be of interest.
Evilblaze
- Guest
Yes, the 125 hour reflux looks nice. But in the lab, I think there will be no problem with it. Somehow we will do it, this is not the risky part.
The white phosphorous is almost free and to work with it... It's not a so big problem I'm still alive(:
There is a big problem for me with the Wurtz-Fittig Reaction: it has a relative low yield and it will produce several different chemicals in the end. Polymers, biphenyls and ect. Maybe I will look for some n-BuLi... I hate it, but this will be the best. And maybe this will be the only version of this reaction with a good yield.
Thanks for the papers!
The white phosphorous is almost free and to work with it... It's not a so big problem I'm still alive(:
There is a big problem for me with the Wurtz-Fittig Reaction: it has a relative low yield and it will produce several different chemicals in the end. Polymers, biphenyls and ect. Maybe I will look for some n-BuLi... I hate it, but this will be the best. And maybe this will be the only version of this reaction with a good yield.
Thanks for the papers!
Evilblaze
- Guest
Hmmm, just found another synth
In the last step, the condensation with EtMgBr, there is used some Mg powder (Aldrich, -50 mesh). I have Merck 100 mesh. This is not the problematic part. The question would be, that my magnesium is 12-15 years old, it was stored properly, the can was opened 3 month ago, but so should I activate it by methanol + iodine or is it enough good?
And what do you think about this synth? It is much more friendly than the n-BuLi and looks better than the Wurtz-Fittig reaction(:
Quote
1,4-Bis(2-chloroethoxy)benzene (9).19 Pyridine (29.4 mL,
364 mmol) was added to a mechanically stirred solution of 1,4-
bis(hydroxyethoxy)benzene ( (Aldrich; 30.0 g, 152 mmol) in
CH2Cl2 (300 mL) at 0 °C. Next, thionyl chloride (25.4 mL, 348
mmol) was added dropwise such that the internal temperature
did not exceed 5 °C.20 This mixture was allowed to warm
gradually to room temperature and was stirred overnight.
Aqueous 2 N HCl (500 mL) was added slowly and the layers
were separated. The aqueous layer was extracted with CH2-
Cl2 (3 75 mL) and the organic extracts were combined. The
pooled organic extracts were then washed with aqueous 2 N
HCl (2 200 mL), water (200 mL), 1 N NaOH (100 mL), and
brine (100 mL). The organic extracts were then dried (MgSO4),
filtered, and evaporated to leave a tan solid that was recrystallized
from ethanol to afford white crystals: 31.4 g, 88%; mp
90-91 °C;
1,4-Bis(2-chloroethoxy)-2,5-dibromobenzene (10).11 Zinc
chloride (38.2 g, 280 mmol) was added to a solution of 9 (27.5
g, 117 mmol) in acetic acid (280 mL). After enclosing the
apparatus in aluminum foil to exclude light, bromine (39.3 g,
246 mmol) dissolved in acetic acid (55 mL) was added dropwise
to the suspension over 1.5 h. The reaction was allowed to stir
overnight, during which time a precipitate had formed. The
reaction was diluted with aqueous saturated sodium thiosulfate
(500 mL) and extracted with CH2Cl2 (5 200 mL). The
organic layers were combined and washed with aqueous 1 N
NaOH (1 200 mL), brine (100 mL), dried (MgSO4), filtered,
and evaporated to leave an off-white solid. Recrystallization
from ethanol afforded a crystalline white product: 50.0 g, 91%;
mp 120 °C
2,3,6,7-Tetrahydrobenzo[1,2-b;4,5-b¢]difuran (7).10 To a
suspension of magnesium powder (Aldrich, -50 mesh, 99+%;
3.7 g, 152 mmol) in anhydrous THF (50 mL) was slowly added
EtMgBr (3.4 mL, 10 mmol, 3 M solution in Et2O).21 An
anhydrous THF solution (125 mL) of the dibrominated compound
10 (20.0 g, 51.0 mmol) was then added dropwise such
that the internal reaction temperature did not exceed 35 °C.
Upon completion of the addition, the reaction was heated at
reflux for 3 h. The reaction was then cooled to room temperature
and carefully poured into cold 1 N HCl (200 mL). Upon
cessation of gas evolution, the mixture was extracted with Et2O
(3 300 mL). The organic layers were combined and washed
with aqueous 1 N NaOH (4 75 mL), brine (50 mL), dried
(MgSO4), filtered, and concentrated by rotary evaporation to
afford a tan solid. This was recrystallized from ethanol to
afford off-white, platelike crystals: 6.5 g, 79%; mp 155 °C
In the last step, the condensation with EtMgBr, there is used some Mg powder (Aldrich, -50 mesh). I have Merck 100 mesh. This is not the problematic part. The question would be, that my magnesium is 12-15 years old, it was stored properly, the can was opened 3 month ago, but so should I activate it by methanol + iodine or is it enough good?
And what do you think about this synth? It is much more friendly than the n-BuLi and looks better than the Wurtz-Fittig reaction(:
Happyman
- Subordinate Wasp
- Posts: 122
Anyone got any info on any of the molecules presented in the attached file? Sorry that they are disorganized.
Also will glycine and benzaldehyde yield 2-amino-1-phenylethanol in an Akabori reaction?
Also will glycine and benzaldehyde yield 2-amino-1-phenylethanol in an Akabori reaction?
Vesp
- Administrator
- Foundress Queen
- Posts: 3,130
Not sure if you searched or not, but I figure i might as well give a link: http://127.0.0.1/talk/index.php?action=search2
See anything useful there? I don't know if its answered or not.
See anything useful there? I don't know if its answered or not.
Happyman
- Subordinate Wasp
- Posts: 122
I see info on a modified Erlenmeyer-Plochl with benzaldehyde and glycine. I see that in an Erlenmeyer-Plochl will produce phenylserine which can be decarboxylized into 2-amino-1-phenylethanol (or a better name, 2-hydroxyphenylethylamine), but that would be an unnecessary extra step if an Akabori reactions works. I see a guy on Drugs-Forum claiming it works, but I see no references.