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

Temperature

140 °C

To a solution of 3,5-dimethoxyaniline (2.53 g, 16.5 mmol) in N-methylpyrrolidinone (10 ml) was added sodium thiomethoxide (2.32 g, 33.1 mmol). The reaction mixture was heated to 140° C. for 2.5 hours and then stirred at ambient temperature for a further 18 hours. The mixture was poured into a saturated solution of NaH2PO4 (50 ml) and then extracted with ethyl acetate. The combined organic layers were filtered through a hydrophobic frit and the solvent was removed under reduced pressure to give a dark red oil. The crude residue was purified by normal phase chromatography, eluting with iso-hexane and increasing amounts of ethyl acetate to give 3-amino-5-methoxyphenol, as a pale yellow solid (1.53 g).

1. extractionextracted with ethyl acetate
2. filtrationThe combined organic layers were filtered through a hydrophobic frit
3. customthe solvent was removed under reduced pressure
4. customto give a dark red oil
5. customThe crude residue was purified by normal phase chromatography
6. washeluting with iso-hexane
7. temperatureincreasing amounts of ethyl acetate

ORD record

ord-fdf8b9c77abb4fea93fd3dedac32d7f2

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993757B2