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ChemicalBook CAS DataBase List 2,6-Dimethoxynitrobenzene 98%

2,6-Dimethoxynitrobenzene 98% synthesis

9synthesis methods
-

Yield: 99%

Reaction Conditions:

with potassium carbonate in acetone for 1 h;Inert atmosphere;Reflux;

Steps:

2,6-Dimethoxynitrobenzene (50) (Scheme 3).
To a solution of 2-nitroresorcinol 49 (4.80 g, 30.9 mmol) in acetone (30 mL) was added K2CO3 (21.39 g, 155 mmol) under nitrogen atmosphere. Dimethylsulfate (8.80 mL, 92.8 mmol) was then added and the mixture obtained was heated to reflux for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The solid obtained was washed with triethylamine and water, then filtered and dried (MgSO4) to give pure compound 5055 (5.6 g, 99%) as a white solid; TLC Rf (EtOAc) = 0.73; 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.88 (s, 6H, 2OCH3), 6.63 (d, J = 8.6 Hz, 2H, ArH), 7.33 (t, J = 8.6 Hz, 1H, ArH).

References:

Ghinet, Alina;Rigo, Benoît;Hénichart, Jean-Pierre;Le Broc-Ryckewaert, Delphine;Pommery, Jean;Pommery, Nicole;Thuru, Xavier;Quesnel, Bruno;Gautret, Philippe [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 20,p. 6042 - 6054] Location in patent:supporting information; experimental part