The synthesis of two β-1 lignol dimers, 1,2-bis-(4-hydroxy-3-methoxyphenyl)-i,3-propanediol (Via) and l-(3-ethoxy-4-hydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (VIb) was performed using the Ivan off Reaction in the key synthetic step. The erythro forms of Via and b were isolated as crystalline solids in yields of approximately 15%, while the threo isomers were obtained as oils. The ratio of threo: erythro isomers was approximately 3:1.