Syntheses of 5-n-Alkylresorcinol dimethyl ethers and 1,14-Bis(3,5-dimethoxyphenyl) tetradecane via β-keto sulphone intermediates

Abstract

Alkylation of 3,5-dimethoxy-α-(methylsulphonyl)acetophenone followed by reduction of the resulting monoalkylated products with zinc and acetic acid afforded the corresponding 5-n-acylresorcinol dimethyl ethers. Hydrogenolysis of 5-n-undecoylresorcinol dimethyl ether, prepared in this way, yielded 5-n-undecylresorcinol dimethyl ether.     Alkylation of 1-(methylsulphonyl)alkan-3-ones with 3,5- dimethoxybenzyl bromide gave a mixture of mono- and di-substituted products. Clemmensen reduction of the monosubstituted products afforded 5-n-alkylresorcinol dimethyl ethers directly.     These reactions have been adapted to provide two syntheses of 1,14- bis(3,5-dimethoxyphenyl)tetradecane.