Resorcinol-mono methyl ether

Bicyclic structures have readily formed from resorcinol mono methyl ether. The... 

Phloroglucinol is readily produced, and with overall 5delds of 50-70%, when starting with 4-chloro resorcinol, which is commercially available. To prepare the mono methyl ether, 4-chloro-3-methoxy phenol can be used. Of course the chlorine atom may also be in one of the two other suitable positions, i.e. the 5- or 6-position, and instead of chlorine in the starting material one of the other halogens may be employed. Useful starting materials thus include 4-chloro resorcinol, 5-chloro resorcinol, 4-bromo resorcinol, 5-bromo resorcinol, 4-chloro-3-methoxy phenol, 5-chloro-3-methoxy phenol, 6-chloro-3-methoxy phenol, 4-bromo-3-methoxy phenol, 5-bromo-3-methoxy phenol, and 6-bromo-3-methoxy... 

Using methyl ethers of di- and tri-hydric phenols, selective mono-demethylation occurs, e.g. resorcinol monomethyl ether is obtained from resorcinol dimethyl ether and sodium ethanethiolate in DMF. An exception is pyrogallol trimethyl ether which afforded pyrogaUol 1-monomethyl ether in high yield. Methylene ethers, such as methylenedioxybenzene, can be quantitatively converted to catechol, via the intermediate formation of ethyl o-hydroxyphenoxymethyl sulphide . 

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