6,7-DICHLOROCHROMAN-4-ONE synthesis
- Product Name:6,7-DICHLOROCHROMAN-4-ONE
- CAS Number:27407-06-3
- Molecular formula:C9H6Cl2O2
- Molecular Weight:217.05
3284-81-9
27407-06-3
The general procedure for the synthesis of 6,7-dichlorochroman-4-one from 3-(3,4-dichlorophenoxy)propionic acid is as follows: 1. 500 mg of 3-(3,4-dichlorophenoxy)propionic acid was suspended in 50 mL of liquid hydrogen fluoride and the reaction system was cooled in a solid carbon dioxide/acetone bath. 2. The reaction mixture was stirred overnight, during which time the cooling bath was not replenished. 3. Upon completion of the reaction, the hydrogen fluoride is removed by a stream of air. 4. The residual solid is dissolved in ether and washed with 10% aqueous sodium carbonate. 5. The organic layer is separated and dried over anhydrous magnesium sulfate, followed by evaporation of the solvent to give 6,7-dichloro-2,3-dihydro-4-one (PCI 65C) of sufficient purity. Product Characterization: PCI 65C was an off-white solid, yield: 350 mg (76%). 1H NMR (CDCl3, 400 MHz) δ: 2.79 (t, 2H), 4.52 (t, 2H), 7.10 (s, 1H), 7.90 (s, 1H). 13C NMR (CDCl3, 100 MHz) δ: 37.4, 67.6, 118.0, 120.2, 120.9, 126.0, 128.3, 140.0, 160.3, 189.9.
3284-81-9
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27407-06-3
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Yield:27407-06-3 76%
Reaction Conditions:
with hydrogen fluorideCooling with acetone-dry ice;
Steps:
VIII.4
[168] Synthesis of 6,7-dichloro-2,3-dihydrochromen-4-one (PCI 65C): Procedure: 500 mg of 3-(3,4-dichlorophenoxy)propionic acid, is stirred in 50 ml. of liquid hydrogen fluoride surrounded by a solid carbon dioxide/acetone bath. This slurry is allowed to stir overnight without replenishing the cooling bath. The hydrogen fluoride is removed by a stream of air. The residual solid was then dissolved in ether and washed with 10% aqueous sodium carbonate solution. The organic layer is dried over anhydrous magnesium sulphate and the solvent is evaporated to give the required chromanone with sufficient purity.[169] PC165C: Off white solid, Yield: 350 mg (76 %); 1H NMR (CDCI3, 400 MHz) in ppm: δ 2.79 (t, 2H), 4.52 (t, 2H), 7.10 (s, 1H), 7.90 (s, 1H); 13C NMR (CDC13, 100 MHz) in ppm: δ 37.4, 67.6, 1 18.0, 120.2, 120.9, 126.0, 128.3, 140.0, 160.3, 189.9;
References:
WO2012/6068,2012,A2 Location in patent:Page/Page column 104-105
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27407-06-3
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27407-06-3
27 suppliers
$239.68/100mg