Pinacol reduction of propiovanillone yielded a, cu'-diethylhydrovanilloin, and this pinacol in the presence of acid underwent rearrangement to the pinacolone 4, 4-di-(4-hydroxy-3- methoxyphenyl~-3-hexanone. Sodium and butanol reduction of the pinacolone yielded the pinacolone alcohol 4, 4-di-(4-hydroxy-3-methoxyphenyl)-3-hexanol, which was heated with aqueous sulfuric acid to yield the desired 3, 3'-dimethoxydiethylstilbestrol by dehydration ...
