| Abstract: | A novel synthesis of methyl 6-acetylsalicylate as a key synthetic intermediate for methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy]-6-1-(methoxyimino)ethyl]benzoate (KIH-6127) was studied, and directed at 6-substituted pyrimidin-2-yl salicylate herbicides and their analogues. Three synthetic approaches were successful: a modification of the Sandmeyer reaction of 6-acetylanthranilate (Method A), a direct ring-opening reaction of 3-methylphthalide using potassium permangamate and magnesium nitrate (Method B), and a regioselective ortho-lithiation of the protected 3-hydroxyacetophenone (Method C). These methods were applicable for the synthesis of various 6-acyl salicylates. |
