9H-Xanthen-9-one, 3,6-dichloro- synthesis

4synthesis methods

Product Name:9H-Xanthen-9-one, 3,6-dichloro-
CAS Number:1556-63-4
Molecular formula:C13H6Cl2O2
Molecular Weight:265.0916

1214-24-0 Synthesis

1214-24-0
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Yield:1556-63-4 81%

Reaction Conditions:

with thionyl chloride for 48 h;Reflux;

Steps:

4.2. Synthesis of 3,6-dichloro-9H-xanthen-9-one (32)

3,6-Dihydroxy-9H-xanthen-9-one (14, 0.200 g, 876 μmol) was dissolved in thionyl chloride (15 ml, 0.21 mol) and the reaction mixture was refluxed for 48 h. After cooling to room temperature, the reaction was carefully quenched with water. The organic phase was extracted with CH2Cl2, washed with saturated Na2CO3 (aq.) and water to give the crude product which was then purified by column chromatography using a mixture of EtOAc/Hexane (3:7) as mobile phase. 3,6-Dichloro-9H-xanthen-9-one (32); White solid (0.188 g, 81% yield); m.p.: 165-168 C; 1H NMR (Lit.43) (300 MHz, CDCl3, δ ppm): 8.25 (2H, d, 3J1,2 = 3J8,7 = 8.6 Hz, H-1, H-8), 7.50 (2H, d, 4J4,2 = 4J5,7 =1.9 Hz, H-4, H-5), 7.36 (2H, dd, 3J2,1 = 3J7,8 = 8.6 Hz and 4J2,4 = 4J7,5 =1.9 Hz, H-2, H-7) ppm.

References:

Rosa;Palmeira;Resende;Almeida;Kane-Pagès;Barreto;Sousa;Pinto [Bioorganic and Medicinal Chemistry,2021,vol. 29,art. no. 115873]

Spiro[benzofuran-3(2H),9'-[9H]xanthen]-2-one, 3',6,6'-trichloro-

112107-57-0
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1556-63-4
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108-43-0 Synthesis

108-43-0
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71641-67-3 Synthesis

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1556-63-4
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