3,5-Dimethoxyaniline → 3-Amino-5-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

3,5-Dimethoxyaniline (9.97 g, 65.1 mmol) and sodium methyl mercaptide (9.1 g, 130 mmol) were dissolved in N-methylpyrrolidinone (60 ml). The reaction mixture was stirred at 140° C. for 1 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated aqueous Na2HPO4. The layers were separated and the organic layer was washed with water, dried over MgSO4 and the solvent was evaporated. The residue was purified by flash chromatography on silica gel eluting with 50% EtOAc/hexanes to afford 3-amino-5-methoxyphenol (5.44 g). MS m/z: 140 [M+H]+

Provenance & Evidence