ChemicalBook CAS DataBase List 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone

2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone synthesis

11synthesis methods

Product Name:2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone
CAS Number:2068-02-2
Molecular formula:C17H14O7
Molecular Weight:330.29

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone

2068-02-2
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Yield: 93%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in tetrahydrofuran;ethanol under 760.051 Torr; for 12 h;

Steps:

3.1.22. 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one (21)
To a solution of 27 (100 mg, 0.20 mmol) dissolved in ethanol (10 ml) and THF (10 ml) was added 10% Pd/C (2 mg) with vigorous stirring. The reaction vessel was then evacuated and the atmosphere replaced with hydrogen. After 12 h, the reaction mixture was filtered through celite and the filtrate concentrated. The crude material was then chromatographed over silica gel (50% ethyl acetate in petroleum ether) to yield 21 (61 mg, 93%) as a yellow solid. Mp 229-230 °C. ¹H NMR (DMSO-d₆, 300 MHz) δ 3.80 (s, 3H, -OCH₃), 3.87 (s, 3H, -OCH₃), 6.37 (d, J = 2.0 Hz, 1H, 6-H), 6.71 (d, J = 2.0 Hz, 1H, 8-H), 6.91 (d, J = 8.4 Hz, 1H, 5'-H), 7.48 (dd, J = 1.8, 8.4 Hz, 1H, 6'-H), 7.59 (d, J = 1.8 Hz, 1H, 2'-H), 9.35 (s, 1H, 3'-OH), 9.77 (s, 1H, 4'-OH), 12.69 (s, 1H, 5-OH). ESI-MS m/z: 331 [M + H]⁺, 353 [M + Na]⁺.

References:

Shi, Zhi-Hao;Li, Nian-Guang;Tang, Yu-Ping;Wei-Li;Lian-Yin;Yang, Jian-Ping;Hao-Tang;Duan, Jin-Ao [European Journal of Medicinal Chemistry,2012,vol. 54,p. 210 - 222] Location in patent:experimental part

117-39-5 Synthesis