Main Index Search Register Login Who's Online FAQ Links | ||||
1 Online, 0 Active | You are not logged in |
|
Novel Discourse | |||
All 7 posts | Subject: Synthesis of 2C-B from Anise Oil (Anethole) | Please login to post | Down | |||||
Rhodium (Chief Bee) 12-09-03 15:22 No 475637 |
Synthesis of 2C-B from Anise Oil (Anethole) (Rated as: excellent) |
|||||||
Anise Oil as Precursor for Phenylethylamine Designer Drugs of the 2C-X Family Dieter Waumans, Noël Bruneel, Jan Tytgat 41st International TIAFT meeting, Poster #104 (https://www.rhodium.ws/pdf/anethole.2c-b.pdf) Introduction Anethole is the main component of anise oil and can be used in the (clandestine) synthesis of 4-methoxy(meth)amphetamine (PM(M)A). It has now been found that anethole can be used as precursor for other phenylethylamines (PEAs) as well. The finding is exemplified for 4-bromo-2,5-dimethoxyphenylethylamine (2C-B) Synthesis Of 2,5-Dimethoxybenzaldehyde A: Anisaldehyde from anethole via oxidative cleavage: 20 g anise oil was suspended in a mixture of 150 mL water and 30 mL conc. sulfuric acid; addition of 55 g sodium bichromate at such a rate that the temperature did not exceed 40°C. The reaction mixture was extracted with 4 x 125 mL toluene and the solvent evaporated. The residual oil was vacuum distilled to yield 9.1 g anisaldehyde. B: O-formyl-4-methoxyphenol: 6 mL anisaldehyde was dissolved in 75 mL dichloromethane (DCM). A mixture of 12 g hydrogen peroxide and 10 mL conc. formic acid was added over 30 min. The reaction mixture was gently refluxed for 21 h. C: 4-methoxyphenol: Evaporating the solvent from reaction mixture B and taking up the residue in 100 mL aqueous NaOH (20%) (25 mL MeOH as co-solvent) yielded 4.1 g 4-methoxyphenol as a white crystalline product after the usual work-up and purification steps. D: Reimer-Tiemann formylation of 4-methoxyphenol: 124.1 g 4-methoxyphenol was dissolved in NaOH solution (320 g NaOH in 400 mL water). In total, 161 mL chloroform was added. The usual work-up and steam distillation yielded 109.8 g of a clear yellow oil that did not solidify upon standing at room temperature (GC/MS: 94% 2-hydroxy-5-methoxybenzaldehyde). E: Methylation of 2-hydroxy-5-methoxybenzaldehyde: The yellow oil from D was used without further purification. A 250 mL RB flask was charged with 100 mL acetone, 14 g anhydrous potassium carbonate and 10 g 2-hydroxy-5-methoxybenzaldehyde; the mixture was brought at reflux temperature and 11 g dimethyl sulfate was added. The reaction was continued for 4 hours. The solvent is evaporated and the crude end product crystallized in cold water. Recrystallization from EtOH/water yielded 8.3 g 2,5-dimethoxybenzaldehyde (GC/MS: 98%+ 2,5-dimethoxybenzaldehyde) Synthesis of 4-Bromo-2,5-Dimethoxyphenylethylamine (2C-B) A: 2,5-dimethoxylphenyl-2-nitroethene A 250 mL RB flask was charged with 16.6 g 2,5-dimethoxybenzaldehyde, 1.6 g NaOAc and 50 mL nitromethane. Refluxing for 4h yielded 14.4 g of the corresponding nitrostyrene after recrystallization. B: 2,5-dimethoxyphenyl-2-nitroethane 5.0 g of 2,5-dimethoxylphenyl-2-nitroethene was added to a solution of 4.0 g sodium borohydride in 100 mL isopropanol. This yielded 4.2 g of a yellow oil after decomposition of the excess borohydride followed by the usual work-up (B). C: 2,5-dimethoxyphenylethylamine (2C-H) The 2,5-dimethoxyphenyl-2-nitroethane was dissolved in 100 mL isopropanol with 8 molar equivalents Zn and 3.5 molar equivalents HOAc (relative to amount of Zn). This yielded 2.0 g of 2,5-dimethoxyphenylethylamine as a faintly yellow oil (C). D: 4-Bromo-2,5-dimethoxyphenylethylamine Hydrochloride (2C-B.HCl) The obtained amine was brominated following Shulgin’s method to yield 2.1 g 2C-B as the hydrochloride salt (D). Conclusion It is possible to synthesize phenylethylamine derivatives different from PMA and PMMA using anethole as precursor. The total yield of 2,5-dimethoxybenzaldehyde from anethole varies between 15-25%. The total yield of 2C-B from 2,5-dimethoxybenzaldehyde amounts to ca 20% (using easily procurable compounds). |
||||||||
hypo (Hive Addict) 12-09-03 16:25 No 475649 |
bitches! | |||||||
that was _my_ idea!! patriots are idiots |
||||||||
Antibody2 (LinguisticBee) 12-09-03 22:17 No 475722 |
the Zn/HOAc redxn again. | |||||||
the Zn/HOAc redxn again. I've heard it mentioned plenty but has anybee on this board actually been sucessful with that one? I'd be curious to know what kind of conditions they were using. We are all just witnesses. |
||||||||
hydroxyindolent (Stranger) 12-12-03 11:08 No 476374 |
Anethole Content of Seed vs. Star Anise Oil | |||||||
Humble Question: Is there a difference in respect to anethole content between star anise and anise seed oil? Star better than seed? If one encounters "anise essential oil" is it safe to conclude it is star anise oil? The authors don't appear to try and purify the essential oil, they just go ahead and oxidize it anyway. What's the concentration of the hydrogen peroxide? 3%? 30%? 35%? Anyone try this method for 2,5 DMBA? Every dimethylsulfate synthesis i've found uses SO3 + dimethyl ether. There must be a better more OTC way. What if methyl alcohol was substituted for ethyl alcohol in the diethylsulfate synth on rhods page? -hydroxy |
||||||||
Rhodium (Chief Bee) 12-12-03 11:56 No 476385 |
Anethole | |||||||
If one encounters "anise essential oil" is it safe to conclude it is star anise oil? That I don't know, but you can be pretty sure that it contains a majority of anethole. The authors don't appear to try and purify the essential oil, they just go ahead and oxidize it anyway. What's the concentration of the hydrogen peroxide? 3%? 30%? 35%? They don't, but I'd reccommend doing that - it is very easy to purify anethol by fractional crystallization as the mp is ~17°C. Every dimethylsulfate synthesis i've found uses SO3 + dimethyl ether. There must be a better more OTC way. UTFSE. Antoncho and Halfapint have discussed this in detail before. The Hive - Clandestine Chemists Without Borders |
||||||||
GC_MS (Hive Addict) 12-15-03 16:00 No 477005 |
anise oil | |||||||
That I don't know, but you can be pretty sure that it contains a majority of anethole. Star anise oil is derived from Illicium verum, a plant economically exploited especially in China and Vietnam for the anethole-rich essential oil. Anise oil itself is derived from Pimpinella anisum, and is sometimes referred to as "sweet anise". Also, there is a difference between anise oil obtained from the seeds and the whole plant. The essential oil derived from the seeds are considered to be of superior quality. When you compare the odours of star anise and ordinary anise oil, you'll find that anise oil has a sweet and pleasant aroma, while the star anise oil has some sort of bitter, sometimes even repellant odour. This repellant odour disappears when you use the anise oil in a diluted form (which it usually is). The world production of star anise oil exceeds that of anise oil. The oil used in the pharmaceutical industry for dental care products etc, usually is star anise oil. Its cost is lower than the ordinary anise oil. Both anise oils have anethole concentrations varying between 80-95%. If "anise oil" is the only information given by the supplier and you happen to be located in the USA or Western Europe, I'd assume that anise oil actually is star anise oil. For the Middle East, Eastern Europe and Asia, anise oil may as well be derived from P anisum. I have no data for the other regions. Advanced clitoris massage specialist. 32 years of experience. PM me for a "sample". |
||||||||
sYnThOmAtIc (Hive Addict) 02-14-04 05:21 No 488554 |
Reaction time | |||||||
How long is the anethole reacted with the dichromate? Is it just carried out untill the addition of the dichromate is over then extraced? Is it allowed to react for some time after? I'm assuming potassium dicrhomate can be used as well in the same manner? Just add and extract? What molar ratio of potassium dicrhomate to anethole be used? |
||||||||