Alkylation of phenol and enol

A convenient catalysed two-phase methoxymethylation of phenols ( 80%) has been described [18], This is an improvement on the standard reaction, which normally requires anhydrous conditions. 1-Naphthol is reported to be 0-mcthylatcd under catalytic conditions with only a minor amount (ca. 3%) of C-methylation at the 2-position [19]. 

The almost instantaneous intramolecular ether formation by reaction of phenoxy anions, generated from the silyl ethers with a stoichiometric amount of tetra-n-butylammonium fluoride, on mesylate esters has been used to synthesize labile benzo-0-2-isocephams ( 90%) [20]. 

5 mmol) are added and the mixture is heated for 4-8 h. H20 (80 ml) is then added and the mixture is extracted with Et20 (3 x 30 ml). The extracts are washed with HzO (3 x 40 ml), dried (Na2S04), and evaporated to yield the aryl ether. 

Method F (polymer-supported reaction) Amberlite IRA-400 (ArO form) (5 g), obtained by washing the resin with aqueous AiONa (0.25 M, 100 ml), followed by H20 (100 ml), is suspended in CH,C12 (20 ml) and refluxed for ca. 12 h. The resin is removed by filtration and is washed with CH2C12 (25 ml). Evaporation of the combined organic solutions yields the diaryloxymethane ( phenols having electron-withdrawing substituents may require 15 h reaction time for maximum yield). 

Method G 2-Amino-3-hydroxypyridine (110 g, 1 mol) in CH2C12 (500 ml) is stirred with aqueous NaOH (40%, 500 ml), the alkylating agent (1.07 mol), and Adogen (5.3 g, 

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