O-Alkylation and Acetylation

The O-alkylation of 3-diethylaminophenol has been effected in 97.5% yield from the phenol in methyl iso-butyl ketone containing powdered potassium carbonate by stirring for SOmins. and after the addition of ethyl bromide, reacting for 3 hours in an autoclave initially at 115-120 C and finally at 140-142X during 5 hours under 5 bar to give 3-diethylaminophenyl 0-ethyl ether (ref.96). 

The selective 0-benzylatk n can be noted in passing, of what might be termed an azaaminophenol, namely 2-amino-3-hydrDxypyridine which took place in 91% yield by reaction with benzyl chbride during 16 hours at ambient temperature in 40% sodium hydroxide/dichloromethane (1 1) in the presence of some Adogen 464 (ref.97). 

4-Acetylaminophenol arKl 0-acetylsalicoyl chloride in chloroform solution treated 

Specific N-acetylation has been effected by the sequential addition of magnesium oxide and acetic anhydride to 2,4-diaminoanisole in methanol solution at 0-5°C during 2 hours to give an 80% yield of 3-amino-4-methoxyacetanilide (ref.99). 

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