3,4'-DIHYDROXYFLAVONE synthesis
- Product Name:3,4'-DIHYDROXYFLAVONE
- CAS Number:14919-49-4
- Molecular formula:C15H10O4
- Molecular Weight:254.24
![4H-1-Benzopyran-4-one, 3-hydroxy-2-[4-(phenylmethoxy)phenyl]-](/CAS/20210305/GIF/102468-65-5.gif)
102468-65-5
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14919-49-4
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Yield: 67%
Reaction Conditions:
with 10% palladium hydroxide on charcoal;hydrogen in ethanol at 60; for 1 h;
Steps:
3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (14a)
To a solution of 11a (100 mg, 0.30 mmol) in CH2Cl2 (5 mL) was added DMDO (9.00 mL, 0.09-0.11 M inacetone) at room temperature under an Ar atmosphere, and the reaction mixture was stirred at 30 °C for1.8 h. Then, the reaction mixture was concentrated under reduced pressure to give a residue including 13a. The residue was purified by silica gel column chromatography (CH2Cl2) to afford 13a (93.6 mg, 89%) asa light brown powder.Spectral data for 13a were in good agreement with those reported in reference.18To a solution of 13a (100 mg, 0.29 mmol) in EtOH (16 mL) was added 10% Pd(OH)2 on charcoal (5 mg)at room temperature, and the reaction mixture was stirred at 60 °C for 1 h under H2 atmosphere. Then, thereaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reducedpressure to give a residue including 14a. The residue was washed with Et2O to give 14a (44 mg, 67%) asa white powder.1H NMR (270 MHz, DMSO-d6): " 10.13 (brs, 1H), 9.32 (brs, 1H), 8.10 (d, J = 9.2 Hz, 2H), 8.09 (d, J =7.9 Hz, 1H), 7.65-7.85 (m, 2H), 7.44 (t, J = 7.9 Hz, 1H), 6.93 (d, J = 9.2 Hz, 2H); 13C NMR (67.8 MHz,DMSO-d6): " 172.6, 159.2, 154.4, 146.2, 137.8, 133.5, 124.7, 124.5, 122.0, 121.4, 118.3; IR (film, cm-1)2980, 2868, 1604, 1557, 1420, 1207, 1107, 1015; MS (FAB): m/z 255 (M+H)+; HRMS (FAB) calcd forC15H11O4+, (M+H)+ 255.0657, found 255.0671.
References:
Hiza, Aiki;Tsukaguchi, Yuta;Ogawa, Takahiro;Inai, Makoto;Asakawa, Tomohiro;Hamashima, Yoshitaka;Kan, Toshiyuki [Heterocycles,2014,vol. 8,# 2,p. 1371 - 1396]
118-93-4
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123-08-0
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14919-49-4
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6889-78-7
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14919-49-4
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87199-17-5
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118-93-4
549 suppliers
$10.00/25g
14919-49-4
51 suppliers
$45.00/250mg
118-93-4
549 suppliers
$10.00/25g
14919-49-4
51 suppliers
$45.00/250mg