ChemicalBook CAS DataBase List 4-Ethoxy-3-nitrobenzoic acid

4-Ethoxy-3-nitrobenzoic acid synthesis

11synthesis methods

Product Name:4-Ethoxy-3-nitrobenzoic acid
CAS Number:59719-77-6
Molecular formula:C9H9NO5
Molecular Weight:211.17

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Yield:59719-77-6 96%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;ethanol;water at 20; for 72 h;

Steps:

6 Reference Example 6 4-ethoxy-3-nitrobenzoic acid

DMF (300 ML) was added to 4-hydroxy-3-nitrobenzoic acid (48.16 g, 0.26 mol) and potassium carbonate (128 g, 0.93 mmol). Ethyl iodide (100 mL, 1.25 mol) was added to the obtained suspension and the suspension was stirred at 90°C for 1 hour. Ethyl iodide (50 mL, 0.63 mol) was further added to the reaction solution and the mixture was stirred overnight, after which ethyl acetate and water were added and the mixture was extracted. The obtained organic layer was washed with 1N hydrochloric acid, dried over magnesium sulfate, and purified by silica gel column to give ethyl 4-ethoxy-3-nitrobenzoate. Ethyl 4-ethoxy-3-nitrobenzoate was dissolved in a mixed solvent of THF (300 mL) and ethanol (200 mL). An aqueous solution of 2N sodium hydroxide (300 mL) was added to the obtained solution at room temperature. After stirring the reaction solution at room temperature for 3 days, 6N hydrochloric acid (120 ML) was added, and the solution was concentrated under reduced pressure to remove organic solvents. The resulting precipitates were collected by filtration, washed with water and dried to give the title compound (53.1 g, yield 96%). 1H NMR (300 MHz, CDC13) 8 ppm: 1.52 (t, J = 7.1 Hz, 3 H), 4.28 (q, J = 7.0 Hz, 2 H), 7.14 (d, J = 9.0 Hz, 1 H), 8.25 (dd, J = 8.9, 2.1 Hz, 1 H), 8.55 (d, J = 2.1 Hz, 1 H).

References:

WO2004/46107,2004,A1 Location in patent:Page 92-93

329-59-9 Synthesis