ChemicalBook CAS DataBase List Emodin-3-methyl ether

Emodin-3-methyl ether synthesis

11synthesis methods

Product Name:Emodin-3-methyl ether
CAS Number:521-61-9
Molecular formula:C16H12O5
Molecular Weight:284.26

518-82-1 Synthesis

518-82-1
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$28.00/25mg

77-78-1
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521-61-9
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$28.00/5mg

Yield:521-61-9 81.3%

Reaction Conditions:

with potassium carbonate in acetone at 60; for 12 h;

Steps:

4.2.1. The preparation of physcion 2 (1, 8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone)

Emodin 2.499 g (9.25 mmol) and K₂CO₃ 1.341 g (9.70 mmol) were solved in 100 mL acetone. The solution was heated to 60 °C and then a solution of 1 mL dimethyl sulfate in 10 mL acetone was added slowly drop by drop. The mixture was stirred at the reflux temperature for 12 h. Then the reaction was stopped and 50 mL water was added to decompose unreacted dimethyl sulfate. The yellow precipitate was separated from water by filtration and the residue was purified by column chromatography with CH₂Cl₂/petroleum ether (v/v = 1:1) elution. A yellow solid was obtained.Yield: 81.3%; yellow solid; mp: 208-210 °C (documental value: 205-207 °C [2]); IR (KBr) ν: 3065, 2987, 2840, 1675, 1633, 1567, 1480, 1325, 1166, 980, 875 cm^-1; ¹H NMR (400 MHz, CDCl₃) δ: 12.31 (s, 1.0H, OH), 12.11 (s, 1.0H, OH), 7.63 (d, J = 1.2 Hz, 1.0H, Ar-H), 7.37 (d, J = 2.8 Hz, 1.0H, Ar-H), 7.08 (d,J = 0.8 Hz, 1.0H, Ar-H), 6.69 (d, J = 2.4 Hz, 1.0H, Ar-H), 3.94 (s, 3.0H, OCH₃), 2.45 (s, 3.0H, Ar-CH₃); ESI-MS m/z 285.1 (M + H)⁺.

References:

Wang, Wenfeng;Bai, Zedong;Zhang, Fengsen;Wang, Conghui;Yuan, Yaofeng;Shao, Jingwei [European Journal of Medicinal Chemistry,2012,vol. 56,p. 320 - 331]

518-82-1 Synthesis

518-82-1
490 suppliers
$28.00/25mg