If you can get p-dimethoxybenzene I'm sure you can get p-methoxyphenol, if not then it could bee made from hydroquinone and benzoquinone in OTC fashion:
Post 516970 (missing)
(azole: "yet another O-monoalkylation of hydroquinone", Novel Discourse) For p-benzoquinone synthesis, read this thread:
Post 374635
(Cyrax: "Yes, you can find it at page 1025 in the 5 th ...", Chemistry Discourse) Formylation of p-MeO-phenol:
Post 478447
(dioulasso: "Formylation w/ Mg(MeO)2 -- translation", Methods Discourse)...or slightly more OTC but messier, a bit unpredictible R-T process:
![](https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000530665-R-T.jpeg)
Once you've introduced the formyl, you could methylate the formed 2-hydroxy-5-methoxybenzaldehyde with DMS as above or methyliodide, you can make it easily in good yield:
Post 301629
(Antoncho: "Two tried-and-true ways to make MeI !", Chemistry Discourse). Now it is possible to alkylate the 2-hydroxy-5-methoxybenzaldehyde with MeI:
Post 348592
(Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)For more examples of alkylations with alkylhalides, see:
Post 223641 (missing)
(IudexK2: "Pihkal: Alkylation of hydroxy-benzaldehydes", Chemistry Discourse)Now you have 2,5-dimethoxybenzaldehyde to go from. It could be coupled with nitromethane (OTC) and reduced to yield 2C-H.
When condensing nitromethane with 2,5-dimeo-benzaldehyde a catalyst is used, for highest yields and purest product employ methylamine. It could bee made from OTC ingridients:
Post 323193
(RoundBottom: "Chromic’s Methylamine.HCl", Methods Discourse) based on:
Post 291265
(Chromic: "just to get you started", Methods Discourse) or Fe/HCl reduction of nitromethane, see;
https://www.thevespiary.org/rhodium/Rhodium/chemistry/eleusis/methylamine27.html#Nitromethane
. For making the MeAm freebase as well as reducing the amount of water in later stage, see:
Post 421720
(Barium: "Not so wet methylamine", Methods Discourse)The catalyst is now ready, and you can start making the nitrostyrene, like described in this post;
Post 419399
(Barium: "High-yielding nitrostyrene catalyst", Methods Discourse).
Now you have some very good and pure nitrostyrene. One step to 2C-H from here is by employing Zn/HCl reduction:
Post 406397
(Sunlight: "Test done", Novel Discourse). This work is based on Leminger's work on mescaline analogs:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/leminger.html
This reduction seem optimal only on 2C-compounds (nitroethene), nitropropenes give ketons as main product.
Save all aqueous phases from reactions involving iodine (swaps, etc), pool, rreduce water and re-generate the expensive iodine w/ H2O2 at pH < 7.
Good luck... And report back...