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

Methyl 4,5-dimethoxy-3-hydroxybenzoate synthesis

9synthesis methods

Product Name:Methyl 4,5-dimethoxy-3-hydroxybenzoate
CAS Number:83011-43-2
Molecular formula:C10H12O5
Molecular Weight:212.2

67-56-1 Synthesis

67-56-1
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1916-08-1
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83011-43-2
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$50.00/250mg

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);⁴⁹¹H 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, 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

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149-91-7 Synthesis