4.6- Dimethyl resorcinol

C0CH2C1 - Preparation by reaction of acetonitrile on 2,4-dimethyl-resorcinol (Hoesch reaction) (93%) [4632],... 

Dimethyl hydroquinone Dimethyl resorcinol Dimethyl octanol Dipentene Diphenyl methane Diphenyl oxide Estragol (methyl... 

Dihydroxy-p-xylene (2 5 Dimethyl-resorcinol, -orcinol, "Xylorcinol). 

Obtained by reaction of acetic anhydride with 4,6-dimethyl-resorcinol in the presence of 45% solution of boron trifluoride etherate at r.t. (15%) [2213] or boron trifluoride-acetic acid complex for 2 h at 100° [2997],... 

Obtained by reaction of propionyl chloride with dimethyl resorcinol-4,6-dicarboxylate in the presence of aluminium chloride in nitrobenzene for 3 h, then at r.t. overnight (75%) [6809],... 

Since the method as given originally leads to 4-alkyl resorcinols which do not produce an active THC, it is here modified to give the 5-alkyl isomers. The method is illustrated for 1.2-dimethyl-heptyI resorcinol which gives a much more active THC than olivetol. 

Reference electrode for electrolytic reduction, 52, 28 Resorcinol dimethyl ether, 50, 52... 

Dimethyl-HeptylResorcinol TET, 23, 77 (1967). According to R. Adams (JACS, 70, 664 (1948), who made this resorcinol back in 1948, it makes a THC 70 times more powerful than the naturally occurring THC when tested on dogs, and is 500 times more potent than natural THC when tested on rats (JMC, 16, 1200 (1973), To come up with the 1,2-dimethyl-heptyl resorcinol, the formula given in the reference must be changed by replacing 2,4-dimethoxy-acetophenone with 3,5-dimethoxy-acetophenone. 

The above methyloctane is demethylated as follows. Mix 40 g of the above product with 100 ml of 48% hydrogen bromide and 320 ml of glacial acetic acid. Heat under reflux for 4 hours, and pour onto ice. Add portions of 10 N sodium hydroxide to the mixture until you get a pH of 4 to 5, then extract with ether. The ether extracts are combined, and extracted with three 150 ml portions of 2 N NaOH. These extracts are combined and acidified with acetic acid, which is then extracted with ether. Dry the combined ether extracts with MgSC 4 and evaporate under reduced pressure (vacuum) to remove the ether. Distill the residue, collecting the fraction boiling at 158-160° at 0.1 mm vacuo to get 20 g of dimetbyl-heptyl resorcinol. Tins demetbylation may be used on olivetol dimethyl ether to demethylate. 

As a first step toward a dopamine-jS-hydroxylase mimic, basket-shaped receptor 17 was functionalized with two sets of bis-[2-(3,5-dimethyl-l-pyra-zolyl)ethyl]amine ligands to give compound 35 (see Scheme 5). Reaction of 35 with Cu(C104,)2-6H20 yielded complex 36 which was fully characterized [39], Ligand system 35 binds dopamine derivative 37 and phloroglucinol (1,3,5-trihydroxybenzene) with association constants of = 60 and 3500 respectively. The affinity of the Cu(I) analogon of 36 for 37 was very similar to that of 36 itself and amounted to Ka = 60 M L Resorcinol is bound in the cavity of the Cu(I) complex with a Xj-value of 2(XX) M". ... 

The use of triethyl orthobut-2-ynoate, MeC=CC(OEt)3, yields 4-methylcoumarins, whilst with dimethyl butynedioate, resorcinol affords methyl coumarin-4-carboxylate in a reaction catalyzed by zinc chloride (69MI22400). The potential elaboration of this approach to coumarins is quite apparent. 

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