ChemicalBook CAS DataBase List 4-HYDROXY-7-METHOXYCOUMARIN

4-HYDROXY-7-METHOXYCOUMARIN synthesis

14synthesis methods

Product Name:4-HYDROXY-7-METHOXYCOUMARIN
CAS Number:17575-15-4
Molecular formula:C10H8O4
Molecular Weight:192.17

552-41-0
575 suppliers
$5.00/1g

105-58-8
447 suppliers
$14.00/25g

17575-15-4
103 suppliers
$22.00/100mg

Yield: 98%

Reaction Conditions:

with sodium hydride in mineral oil at 0 - 85; for 14 h;

Steps:

4-hydroxy-7-methoxy-2H-chromen-2-one (4)
Solutionof 1-(2-hydroxy-3,4-dimethylphenyl)ethanone(5g; 0.03 mol) in diethylcarbonate (35 mL) was added dropwise to asuspension of NaH (60% dispersion in mineral oil) (5 g; 0.21 mol) indiethylcarbonate (25 mL) at 0 ^oC. The resulting mixture was heatedat 85 ^oC for 14 h after which it was cooled first to rt and then to0 ^oC. Water was then carefully addeddropwise to quench residual NaH. The remaining diethylcarbonate was extractedinto diethyl ether (3 x 50 mL). The aqueous phase was carefully acidified to pH3 with 2N HCl (significant foaming occurred). The resulting precipitated solidwas collected by filtration, washed sequentially with water followed bypetroleum ether (40-60 ^oC:3 x 50 mL), and then dried in a 90 ^oC oven overnight to yield whitecrystals (5.67 g; 98%). ¹H-NMR(DMSO-d₆) (δ/ppm): 12.38(1H, bs, OH-4), 7.72 (1H, d, H-5, J=8.4Hz), 7.00-6.91 (1H, m, H-6), 6.95 (1H, s, H-8), 5.46 (1H, s, H-3), 3.85 (1H, s,OCH₃). ¹³C-NMR (DMSO-d₆) d/ppm: 166.0 (C-4), 162.9 (C-1), 162.2 (C-7),155.4 (C-10), 124.3 (C-5), 111.8 (C-6), 108.9 (C-11), 100.5 (C-8), 88.5 (C-3),55.8 (OCH₃).

References:

Andjelkovic, Uroš;Antolović, Roberto;Bracanović, Sara;Cetina, Mario;Jelić, Dubravko;Kraljević Pavelić, Sandra;Vinter, Adrijana;Wittine, Karlo;Wittine, Ozren [Bioorganic and medicinal chemistry letters,2020,vol. 30,# 18] Location in patent:supporting information