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CAS No. : | 10463-20-4 | MDL No. : | MFCD00007122 |
Formula : | C8H7NO5 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | QBHBHOSRLDPIHG-UHFFFAOYSA-N |
M.W : | 197.15 | Pubchem ID : | 447364 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 0.5h; | 2-(4-hydroxy-3-nitrophenyl)acetic acid (10.0 g, 50 mmol) was dissolved in N,N-dimethylformamide (100 mL) and potassium carbonate (21.0 g, 152.2 mmol) was added into the solution. Methyl iodide (21.0 g, 147.9 mmol) was then added. The reaction mixture was warmed to 50 C. and reacted for 30 min. TLC showed the reaction was completed. The reaction mixture was slowly added into 300 mL of water, filtered, and the solid was washed with water and dried in vacua to give methyl 2-(4-methoxy-3-nitrophenyl)acetate (11.2 g, 49.8 mmol, yield: 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.81 (d, J=2.4 Hz, 1H), 7.57 (dd, J=2.4 and 8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 3.91 (s, 3H), 3.75 (s, 2H), 3.63 (s, 3H); MS: 226.3 [M+H]+. |
In N,N-dimethyl-formamide; | (1) A mixture of 4-hydroxy-3-nitrophenylacetic acid (10 g, 50.7 mmol), sodium hydride (2.6 g, 0.11 mol), iodomethane (15.6 g, 0.11 mol) and N,N-dimethylformamide (170 ml) was stirred at room temperature overnight. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with 1 N aqueous sodium hydroxide solution, 5% potassium hydrogen sulfate, saturated aqueous sodium hydrogen sulfate and saturated saline, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1) to obtain methyl 2-(4-methoxy-3-nitrophenyl)acetate (10.4 g, 46.2 mmol, 91%) as colorless needles. Melting point 101-102 C. IR numax (KBr) cm-1: 1730 (C=O). 1H-NMR (CDCl3) delta: 3.626 (2H, s), 3.718 (3H, s), 3.960 (3H, s), 7.062 (1H, d, J=8.8 Hz), 7.478 (1H, dd, J=2.2, 8.8 Hz), 7.795 (1H, d, J=2.2 Hz). Elemental analysis (C10H11NO5) Cal'd: C, 55.58; H, 5.30; N, 4.96. Found: C, 53.44; H, 4.87; N, 5.98. |
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