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27407-06-3

6,7-DICHLOROCHROMAN-4-ONE synthesis

3synthesis methods
-

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