3- methoxybenzene- sodium

Evidently, hydrogen facilitates the nucleophilic replacement of fluorine by the methoxy group more efficiently than the halogens fluorine < chlorine < bromine < iodine < hydrogen.83,84 1,2,4,5-Tetrafluorobenzene when treated with sodium methoxide in methanol yields 1,2,4-tri-fluoro-5-methoxybenzene (7).83... 

Exercise 22-35 Explain why sodium in liquid ammonia reduces methoxybenzene (anlsole) to 1-methoxy-1,4-cyclohexadiene, whereas it reduces sodium benzoate to sodium 2,5-cyclohexadienecarboxylate ... 

However, neither copper(I) iodide nor photostimulation are absolutely necessary for the arylation of benzenetellurolate. Lithium benzenetellurolate and 1,2-bromoiodobenzene condensed in tetrahydrofuran at 20° to form 1,2-bis[phenyltelluro]benzene in 32% yield3. Sodium benzenetellurolate condensed similarly with l-chloro-2,4-dinitrobenzene at 20° in tetrahydrofuran/aqueous sodium hydroxide in the presence of a phase-transfer reagent. In this case 2,4-dinitrophenyl phenyl tellurium (m.p. 134°) was isolated in 30% yield4. Lithium methanetellurolate was arylated in tetrahydrofuran by iodobenzene5, 1,2-dibromobenzene, and l-bromo-2-methoxybenzene at 20°3. 

When the sodium salt of a phenol is treated with an alkyl halide or an alkyl sulfate, 0-alkylation occurs and an ether is formed, usually in good yield. Methyl ethers such as anisole (methoxybenzene) can also be formed in excellent yield by treatment of a phenol with diazomethane (Scheme 4.8). 

A Study of the Catalytic Hydrogenation of Methoxybenzenes over Platinum and Sodium Catalysts... 

Draw the radical anion intermediate formed when methoxybenzene (anisole see Chapter 21, Section 21.2) is treated with sodium in ethanol and ammonia (Birch reduction), and draw all resonance structures. Based on stability of the radical anion product, suggest the final product of this reduction. 

Method Five, Feofilaktov et al. (275). p-Methoxybenzene + formaldehyde -f- ZnClj + HCl - p-methoxybenzyl chloride (A). (A) + ethyl acetoacetate + sodium ethyl p-methoxybenzylacetoacetate (B). (B) -I- phenyl diazonium chloride p-methoxyphenylp3rruvic acid phenyl-hydrazone -> a-amino-j8-p-methoxyphenylpropionic acid -> tyrosine. An over-all 3rield of 27% was reported. 

Also obtained by reaction of sodium methoxide with l-ethoxy-4-(l, 2-dibromopropyl)-2-methoxybenzene in methanol [7100,7240],... 

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