The Lewis accid used in the alkylation might cleawe the methoxyethers.
the Friedel-Crafts alkylation w/alcohols doesn't require a lewis acid.. I doubt AlCl3 would cleave the ethers anyhow as long as the solvent is right, otherwise bees wouldn't be having so many problems cleaving eugenol/vanillin's methoxy groups.
PErsonal I prefere bromination and the BuLi and RBr
you must like performing reactions at -70degC under an inert atmosphere and anhydrous conditions, eh? not to mention the hassle obtaining butyllithium.
Saddam_Hussein - excuse my ignorance, but by what means is this aldehyde "OTC"?
Post 530676 (https://www.thevespiary.org/talk/index.php?topic=9336.msg53067600#msg53067600)
(Captain_America: "OTC 2C-H", Methods Discourse)Post 530920 (https://www.thevespiary.org/talk/index.php?topic=9947.msg53092000#msg53092000)
(Nicodem: "The best spices for DOM", Methods Discourse). Nicodem had quite an idea for OTC DOM synthesis.Patent US2401608 (http://l2.espacenet.com/dips/viewer?PN=US2401608&CY=gb&LG=en&DB=EPD)
to obtain o-cresol; briefly discussed in thisPost 505367 (https://www.thevespiary.org/talk/index.php?topic=9940.msg50536700#msg50536700)
(psyloxy: "H2O2 o-cresol to 2,5-dihydroxytoluene, 98%", Methods Discourse)Patent IE904369 (http://l2.espacenet.com/dips/viewer?PN=IE904369&CY=gb&LG=en&DB=EPD)
describes the preparation of toluhydroquinone from o-cresol. o-cresol is acetylated (the patent states that even plain old acetic acid will work, though the examples only use acetyl chloride) to 4'-hydroxy-3'-methyl-acetophenone catalysed by HF. The acetophenone is then oxidised to toluhydroquinone via alkaline H2O2.Post 505784 (https://www.thevespiary.org/talk/index.php?topic=9231.msg50578400#msg50578400)
(psyloxy: "K2S2O8 oxidation of o/m-cresol to toluhydrochinone", Methods Discourse)I'm also wondering if that ortho-alkylation of phenols could be applied directly to hydroquinone to get toluhydroquinone, and if paraformaldehyde could be used in this process or if depolymerization or the use of formalin as in the patent would be necessary..
My thought here: rather use p-MeO-phenol than hydrochinone.
--psyloxy--