Williamson ether synthesis
8 real reactions from the literature, on phenols, phenoxides, α-halo acids and secondary alcohols. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Williamson ether synthesis: 4-aminophenol with NaH; DMF gives 4-ethoxyaniline (the aryl alkyl ether). 78% yield.
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Williamson ether synthesis: chloroacetic acid (an α-halo acid) with NaOCH2CH3 gives sodium ethoxyacetate (the ether).
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Williamson ether synthesis: guaiacol (a phenol) with K2CO3 gives 1-methoxy-2-prop-2-enoxybenzene (the allyl aryl ether).
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Williamson ether synthesis: a phenoxide with NaOH, H2O, Δ gives 3-bromopropoxybenzene (the aryl alkyl ether).
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Williamson ether synthesis: a secondary alcohol and chloroacetic acid (an α-halo acid) with Na (2 equiv), Δ; then H2O / HCl gives the ether.
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Williamson ether synthesis: 2-acetylhydroquinone (a phenol) with CH3I, K2CO3; acetone, Δ gives 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (the aryl alkyl ether).
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Williamson ether synthesis: a phenoxide with CH3CH2OH, Δ gives 3-phenoxy-1,2-propanediol (the aryl alkyl ether).
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Williamson ether synthesis: chloroacetyl chloride (an α-halo acid chloride) and D(-)-leucinol (a primary alcohol) with 1) K2CO3 / H2O / THF; 2) tBuOK / tBuOH; 3) aq HCl workup gives the cyclic ether.