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CAS No. : | 20876-30-6 | MDL No. : | MFCD06659779 |
Formula : | C9H9NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XCGMUHYKYLADKO-UHFFFAOYSA-N |
M.W : | 211.17 | Pubchem ID : | 11413180 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
100% | Stage #1: at 90℃; for 1 h; Stage #2: at 85℃; for 1 h; |
Intermediate 49 : ^-methoxy-l-nitrophenvDacetic acid; <n="74"/>A solution of diethyl (4-methoxy-2-nitrophenyl)malonate (1.1 g; 3.53 mmol; 1 eq) in a mixture of EtOH (25 mL) and sodium hydroxide (25 mL; 1 M; 25 mmol; 7.07 eq) is heated for 1 h at 900C. The solvents are removed under reduced pressure and the orange-yellow powder is suspended in THF (2OmL). After cooling down to O0C, 5M HCl (2OmL) is added. The reaction mixture is refluxed at 85°C for 1 h. After cooling down to room temperature, the 2 phases are separated and the organic phase is dried over MgSO4. The aqueous phase is treated twice with EtOAc (5OmL) and the combined organic phases are dried over MgSO4 then concentrated to dryness to afford 850 mg (100percent) of the title compound as a brown solid. 1H NMR (DMSO-d6) δ 8.20-8.10 (m, IH), 7.45 (d, J= 3.0 Hz, IH), 7.05 (d, J= 8.0 Hz, IH), 6.95 (dd, J= 8.0, 3.0 Hz, IH), 3.78 (s, 2H), 3.67 (s, 3H). HPLC (max plot) 89percent; Rt 2.54 min. LC/MS: (ES+): 229.0 (M+NH4+). |
82% | for 13 h; Heating / reflux | Diethyl 4-methoxy-2-nitrophenylmalonate (1.1 g, 36 mmol) in 5 mL of 6 N hydrochloric acid were refluxed for 13 hours with stirring. The reaction was cooled to room temperature and the brown precipitate collected and washed with water. The precipitate was dissolved in 1.5 mL of 2 N sodium hydroxide and extracted with 1 mL of ethyl acetate. The aqueous layer was refluxed with 0.1 g of Darco-G60, hot filtered, and acidified with 0.5 mL of 6 N sulfuric acid. The filtrate was cooled in the refrigerator and the tan precipitate collected by vacuum filtration, washed with water and dried under vacuum to give 0.6 g (82percent yield) of 4-methoxy-2-nitrophenylacetic acid. |
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