The Problem for me is getting those chemicals. Your site has stuff on vanillin that looks easy enough. I dont kow the physics of whether it would work to substitue isoeugenol. It would be best if 3-methoxy-4-hydroxyamphetamine could be used as the starting point (none of the ethylated benzene would be wasted in oxone oxidation). Here is what I was wondering:
In this article, from rhodiums page, vanillin is iodinated:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/iodovanillin.html
-----------------------------------------------------------
5-Iodovanillin (JCS 3740-3741 (1958))
12.6g Iodine was added in 4 portions during 30 min to a rapidly stirred suspension of 7.5g vanillin in 200mL H2O containing 5g NaHCO3 and 10g KI. Stirring was continued for 3h and the mixture left overnight. The filtered product was washed with dilute Na2S2O3 and H2O and dried at 45°C (11.8g, mp 175°C). Crystallised from EtOH(aq), it had mp 180°C.
------------------------------------------------------------
vanillin mol wt. 152.14
isoeugenol mol wt. 164.20
eugenol amphetamine mol wt. 181.22
so i would guess:
5-iodo-isoeugenol (or eugenol amphetamine)
12.6g Iodine was added in 4 portions during 30 min to a rapidly stirred suspension of 8.09g isoeugenol (or 13.4g eugenol amphetamine) in 200mL H2O containing 5g NaHCO3 and 10g KI. Stirring was continued for 3h and the mixture left overnight.
The filtered product was washed with dilute Na2S2O3 and H2O and dried at 45°C (Something else would probably be necessary)
yielding 5-iodo-isoeugenol (mol wt. 291.1) (or 3-methoxy-4,5-dihydroxyamphetamine (mol wt. 308.12))
then another article says
https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html
-----------------------------------------------------------
3,5-Dimethoxy-4-Hydroxybenzaldehyde (Syringaldehyde)
In a two-necked round-bottomed flask equipped with a Claisen, and a thermomether into the solution, is dissolved 4.9g Na in 100mL dry methanol. After distilling off 30ml methanol, a solution of 17,9g bromovanilin and 3g Cu(I)Br in 50mL DMF is added in one portion. The distillation is continued until the reaction mixture reaches 100°C (takes app. 1-1.5 h. total methanol distilled off is 80mL). The reaction mixture is poured into 200mL 3M HCL/ice, extracted with 2*75mL EtOAc, the EtOAc is washed with 2*50mL water, dried with MgSO4 and evaporated. Mp.108°C (rec. from ethanol) TLC Rf 0,35 EtOAc:P 1:1
------------------------------------------------------------
If you substitute iodoisoeugenol or iodo eugenol amphetamine for bromovanillin:
3,5dimethoxy-4-hydroxypropenylbenzene (or 3,5DM-4OHA)
In a two-necked round-bottomed flask equipped with a Claisen, and a thermomether into the solution, is dissolved 4.9g Na in 100mL dry methanol. After distilling off 30ml methanol, a solution of 22.4g 5-iodo-isoeugenol (or 23.7g 3-methoxy-4hydroxy-5-iodo amphetamine) and 3g Cu(I)Br in 50mL DMF is added in one portion. The distillation is continued until the reaction mixture reaches 100°C (takes app. 1-1.5 h. total methanol distilled off is 80mL). The reaction mixture is poured into 200mL 3M HCL/ice, extracted with 2*75mL EtOAc, the EtOAc is washed with 2*50mL water, dried with MgSO4 and evaporated.
this could then be reacted with allyl bromide to yield 3C-AL
http://www.erowid.org/library/books_online/pihkal/pihkal002.shtml
1. I know in pihkal it said that 34dma was difficult to brominate would eugenol amphetamine be hard to iodinate.
2. In step 2 could an equimolar amount of lithium (1.47g) be used instead of Na(4.9g)
3. Should Cu(I)I be used instead of Cu(I)Br
4. If nothing else, could 3-methoxy-4-ethoxy be formed by ethoxylating the amphetamine, or do you have to do that as a phenylpropanoid.
