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

Temperature

140 °C

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]+

1. temperatureAfter cooling to room temperature
2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous Na2HPO4
3. customThe layers were separated
4. washthe organic layer was washed with water
5. dry with materialdried over MgSO4
6. customthe solvent was evaporated
7. customThe residue was purified by flash chromatography on silica gel eluting with 50% EtOAc/hexanes

ORD record

ord-d4fd153c63bb4d4387a79c5f53a4f90f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765779B2