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ChemicalBook CAS DataBase List Methyl 4,5-dimethoxy-3-hydroxybenzoate
83011-43-2

Methyl 4,5-dimethoxy-3-hydroxybenzoate synthesis

9synthesis methods
-

Yield:83011-43-2 97%

Reaction Conditions:

with sulfuric acid at 20; for 24 h;

Steps:

Methyl 3-hydroxy-4,5-dimethoxybenzoate (70) (Scheme 6).
To a solution of acid 69 (3.0 g, 151.4 mmol) in methanol (30 mL) was added sulfuric acid (0.5 mL). The solution was stirred at room temperature for 24 h, after which time the solvent was removed in vacuo. The crude residue was partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc, and the combined organic extracts were washed with water then brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/n-heptane) to give pure compound 70 (3.13 g, 97%) as an off-white solid; mp (EtOAc/n- heptane) 68 °C (lit. 72-74 °C);49 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.89 (s, 3H, OCH3), 3.91 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 5.82 (s, 1H, ArOH), 7.20 (d, J = 2.0 Hz, 1H, ArH), 7.31 (d, J = 2.0 Hz, 1H, ArH). IR ν cm-1: 756, 995, 1006, 1110, 1162, 1200, 1270, 1356, 1594, 1704, 3403.

References:

Ghinet, Alina;Rigo, Beno?t;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

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