Sulfamic Acid → 2-(3-Methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) and sulfamic acid (3 mmol) in 7 mL of H2O:THF:DMSO (20:10:1) at 0° C. was treated with NaClO2 (3 mmol) in 1 mL of H2O. The reaction mixture was stirred for 20 min at 0° C. The reaction was diluted with EtOAc (30 mL), washed with saturated aqueous NH4Cl (2×15 mL) and saturated brine, and dried (Na2SO4). Evaporation of the solvents under reduced pressure and further purification by column chromatography gave 2-(3-methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (85%).

Provenance & Evidence