Hydrochloric Acid → 4,5-Dimethoxy-2-nitrophenol

To a solution of 4,5-dimethoxy-2-nitro-benzaldehyde (3.75 g, 14.2 mmol) in dichloromethane (75 mL) at 0° C. under a nitrogen atmosphere was added meta-chloroperoxybenzoic acid (75% purity, 4.90 g, 28.4 mmol), then, trifluoroacetic acid (1.05 mL, 14.2 mmol). The reaction was stirred at room temperature for 18 h, then recooled to 0° C. Excess reagent was quenched with 5% sodium bisulfite solution and the precipitate was removed by filtration, washing with dichloromethane. The organic phase of the filtrate was washed with sodium bicarbonate and brine, was dried (sodium sulfate), and was evaporated to provide a yellow solid. This intermediate was suspended in methanol (50 mL), treated with 2N NaOH (16 mL, 32 mmol), and was stirred at room temperature for 1 h. The reaction was acidified with 1N HCl and was filtered, washing with methanol to provide 4,5-dimethoxy-2-nitro-phenol (2.00 g, 71% yield) as a bright yellow solid. 1H-NMR (CDCl3, 500 MHz) 11.0 (s, 1H), 7.39 (s, 1H), 6.48 (s, 1H), 3.90 (s, 3H), 3.83 (s, 3H) ppm; MS (FIA) 197.9 (M−H); HPLC (Method A) 3.357 min.

1. customrecooled to 0° C
2. customExcess reagent was quenched with 5% sodium bisulfite solution
3. customthe precipitate was removed by filtration
4. washwashing with dichloromethane
5. washThe organic phase of the filtrate was washed with sodium bicarbonate and brine
6. dry with materialwas dried (sodium sulfate)
7. customwas evaporated
8. customto provide a yellow solid
9. stirringwas stirred at room temperature for 1 h
10. filtrationwas filtered
11. washwashing with methanol

ORDレコード

ord-53e0f2e0a77f4107a04aa157a1df77db

出典データセット

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07279469B2