Sodium Hydroxide → Methyl hydrogen 2-nitroterephthalate

Participants

Reaction Steps

To a stirred solution of di-methyl nitroterephthalate ((5), 12g, 50 mMol) in dioxane (100 mL) at room temperature was slowly added dropwise aq. 1N NaOH (50 mL) over 30 minutes. After stirring for 16 h at room temperature the reaction was diluted with water, washed with ether, acidified with aq. 1N HCl (50 mL) then extracted with 10% n-BuOH in ethyl acetate (2×100 mL). After drying (MgSO4) over ethyl acetate and evaporation under reduced pressure the resulting residue was purified by flash chromatography on silica gel eluted with (98:2:0.1) CHCl3, MeOH, HOAc to give product (6) (8.07 g, 72%) as a white solid.

Provenance & Evidence