Acetonitrile → Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}-5-nitrobenzoate

To a mixture of methyl 3-hydroxy-2-{[2-(methyloxy)ethyl]oxy}-5-nitrobenzoate (4.4 g, 16.2 mmol), potassium carbonate (4.5 g, 33 mmol) and acetonitrile (100 mL) was added 1-bromo-2-(methyloxy)ethane (2.5 mL, 24 mmol). The resulting mixture was heated at reflux 18 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 mL), filtered and concentrated. The residue was then diluted with ethyl acetate (100 mL) and washed with 5% sodium hydroxide solution, water and brine (100 mL each), dried over sodium sulfate, filtered, concentrated, and the residue was chromatographed (silica gel, 30-50% ethyl acetate-hexane) to provide to give methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}-5-nitrobenzoate, (4.9 g, 14.8 mmol, 91% yield). 1H NMR (400 MHz, CDCl3): 8.27-8.26 (d, 1H), 7.92-7.91 (d, 1H), 4.37-4.35 (m, 2H), 4.27-4.25 (m, 2H), 3.94 (s, 3H), 3.83-3.81 (m, 2H), 3.77-3.74 (m, 2H), 3.45 (s, 3H), 3.42 (s, 3H).

1. temperatureThe resulting mixture was heated
2. temperatureat reflux 18 hour
3. filtrationfiltered
4. concentrationconcentrated
5. additionThe residue was then diluted with ethyl acetate (100 mL)
6. washwashed with 5% sodium hydroxide solution, water and brine (100 mL each)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customthe residue was chromatographed (silica gel, 30-50% ethyl acetate-hexane)
11. customto provide

ORD record

ord-9ae8ea5a33fa4574830cbbc51f6db1dc

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872014B2