Since the begining of The Hive there have been several attempts to synthesize this amazing psychedelic fom easily obtainable chemicals. Most of them strated by monomethylation of hydroquinone, followed by Reimer-Tiemann formylation of thus obtained p-methoxyphenol. The isolated 2-OH-5-MeO benzaldehyde is then methylated to get the much desired product, 2,5-dimethoxybenzaldehyde. The true pioneer of this method is Antoncho, who has made several attempts to prepare that damn aldehyde, bu AFAIK he wasn't very successful
(feel free to correct me if I'm wrong). The problem with this method is major tar formation during formylation if one does not follow the procedure correctly. Therefore I propose a new, kitchen (as Antoncho would say
) synthesis of 2,5-dimethoxybenzaldehyde.
Step 1: Bromination of SalicylaldehydeLugh has posted an article in
Post 511284
(lugh: "5-bromosalicylaldehyde", Chemistry Discourse), but "deutsche sprache" is kinda like ancient hieroglyphics for me. I briefly understand what they say and as far as I can see it is a standard Br
2/GAA bromination. One could therefore easily use a procedure for brominating vanillin as an example. I believe (or should I say, hope) that hydroxyl group would push the bromine to the para position, so the main product would be 5-bromo-2-hydroxybenzaldehyde (5-Br salicylaldehyde).
Patent US4551558
- Bromination of substituted benzaldehydes
https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html
Step 2: Methoxylation of 5-bromosalicylaldehydehttps://www.thevespiary.org/rhodium/Rhodium/chemistry/arylhalide.methanolysis.cu-etoac.html
Post 503332
(Rhodium: "Methoxylation of Aryl bromides cat. by Cu(II)-CO2", Chemistry Discourse)Post 511008
(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)Post 477850
(Rhodium: "ArBr --NaOMe/Cu(I)--> ArOMe", Chemistry Discourse)Preparation of alkali metal alkoxides:Post 257912
(Antoncho: "Alkali metal alkoxides: finally, OTC!", Novel Discourse)Post 512006
(Nicodem: "The patents work", Newbee Forum)Step 3: Methylation of 2-OH-5-MeO benzaldehydeThis step is probably the one that is the most widely covered at The Hive. Here are some links, just to get the impression of what I am talking about.
Post 348592
(Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)Post 511704
(Aurelius: "O-Alkylation Agents: Synthesis and Use", Methods Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
- Trimethyl phosphate alkylation of phenolic aldehydes
You all know how the things go from here. I wold be thankful if bees would now reply to this post and share their thoughts on this project.