4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one

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Products Intro: Product Name:4-Hydroxy-5-methoxy-2H-chromen-2-one
CAS:53666-76-5
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4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one Basic information
Product Name:4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one
Synonyms:4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one;4-Hydroxy-5-methoxy-2H-chromen-2-one;2H-1-Benzopyran-2-one, 4-hydroxy-5-methoxy-
CAS:53666-76-5
MF:C10H8O4
MW:192.17
EINECS:
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Mol File:53666-76-5.mol
4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one Structure
4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one Chemical Properties
Melting point 155 °C(Solv: ethanol (64-17-5))
Boiling point 403.1±45.0 °C(Predicted)
density 1.412±0.06 g/cm3(Predicted)
pka4.50±1.00(Predicted)
Safety Information
MSDS Information
4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one Usage And Synthesis
Synthesis4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one is obtaned by 2-Hydroxy-5-methoxy-acetophenone with sodium hydride in diethyl carbonate.2-Hydroxy-5-methoxy-acetophenone (1.50 g, 9.03 mmol) in diethyl carbonate (8.3 ml) was added dropwise into a suspension of sodium hydride (60% dispersion in mineral oil, 1.81 g, 45.2 mmol) in diethyl carbonate (8.3 ml) and heated under reflux at 100 ?C for 3 hours. The resultant mixture was left to cool to 0 ?C in an ice bath and quenched by dropwise addition of water until effervescence ceased. The aqueous layer was washed with diethyl ether (3 × 16 ml) then acidified using concentrated hydrochloric acid to pH 1. The precipitate was filtered and washed with water, followed by petroleum ether and left to dry overnight at 90 ?C to give the title compound as a colourless solid (902 mg, 52%): mp: 150 – 153 ?C (Lit.: 155 ?C); vmax/cm-1 3207bw (O-H), 1727s (C=O), 1655m (C=C), 1606s (aro. ring C=C); δH (300 MHz; DMSO-d6) 11.34 (1H, br. s., OH), 7.57 (1H, t, J 8.4, C(7)H), 6.95 (2H, d, J 8.4, C(6)H and C(8)H), 5.51 (1H, s, C(3)H), 3.90 (1H, s, OCH3); δC (75 MHz; DMSO-d6) 167.2 (Ar-C), 161.4 (Ar-C), 157.3 (Ar-C), 155.2 (Ar-C), 133.0 (Ar-CH), 109.2 (Ar-CH), 106.8 (Ar-CH), 105.0 (Ar-C), 90.8 (C(3)H), 56.5 (OCH3); m/z (-ES) 191 (100%, [M-H]-).
4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one Preparation Products And Raw materials
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