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1843-90-9

2,3-DIHYDRO-8-HYDROXY-4H-1-BENZOPYRAN-4-ONE synthesis

3synthesis methods
20351-79-5 Synthesis
8-Methoxy-4-chromanone

20351-79-5
62 suppliers
$31.00/100mg

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Yield:1843-90-9 56%

Reaction Conditions:

aluminium trichloride in 5,5-dimethyl-1,3-cyclohexadiene;

Steps:

R.37 2,3-Dihydro-8-hydroxy-4H-1-benzopyran-4-one

Reference Example 37 2,3-Dihydro-8-hydroxy-4H-1-benzopyran-4-one 2,3-Dihydro-8-methoxy-4H-1-benzopyran-4-one (7.59 g, 42.4 mmol) was dissolved in xylene (80 mL) followed by addition of anhydrous aluminum chloride (11.4 g, 85.5 mmol), and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was poured into iced water and extracted with ethyl acetate. The organic layer was washed with 1N-hydrochloric acid and saturated aqueous sodium chloride solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from methanol-ethyl acetate-diethyl ether to provide 3.94 g of the title compound. Yield 56%. m.p. 93-96° C. 1H-NMR (CDCl3) δ: 2.86 (2H, t, J=6.4 Hz), 4.63 (2H, t, J=6.4 Hz), 5.72 (1H, s), 6.93 (1H, t, J=8.0 Hz), 7.14 (1H, dd, J=7.8, 1.6 Hz), 7.44 (1H, dd, J=7.8, 1.6 Hz).

References:

US6248766,2001,B1