Potassium Carbonate → O-ethyl O-(xanthen-9-one-4-yl) (2,4,6-trichlorophenyl)phosphonate

HRID 1995380Notes

Reaction equation

HRID 1995380 reaction equation
[OH:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:25]=1[P:32](Cl)(=[O:36])[O:33][CH2:34][CH3:35]>C(#N)C>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:25]=1[P:32](=[O:36])([O:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[O:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6114284-HydroxyxanthoneHCID 53729853O-Ethyl (2,4,6-trichlorophenyl)phosphonochloridate

Product 1

HCID 54313362O-ethyl O-(xanthen-9-one-4-yl) (2,4,6-trichlorophenyl)phosphonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Hydroxyxanthen-9-one (0.01 mole), acetonitrile (25 ml) and potassium carbonate (0.01 mole) are charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer. O-Ethyl (2,4,6-trichlorophenyl)phosphonochloridate (0.01 mole) in acetonitrile (6 ml) is added dropwise, with stirring, at room temperature. The reaction mixture is stirred for a period of about 48 hours at a temperature of from about 35° C. to 50° C. It is then cooled to room temperature and filtered. Solvent is stripped from the filtrate using a rotary evaporator (70° C., 15 mm Hg). The devolatilized residue is redissolved in 1/1 v/v chloroform/cyclohexane (25 ml). This solution is then slurried with silica gel (2 grams) at room temperature for a period of about 2 hours, then filtered. Solvent is stripped from the filtrate using a rotary evaporator to yield the desired product O-ethyl O-(xanthen-9-one-4-yl) (2,4,6-trichlorophenyl)phosphonate.

Workup

  1. customfitted with a mechanical stirrer
  2. stirringThe reaction mixture is stirred for a period of about 48 hours at a temperature of from about 35° C. to 50° C
  3. temperatureIt is then cooled to room temperature
  4. filtrationfiltered
  5. customa rotary evaporator (70° C., 15 mm Hg)
  6. dissolutionThe devolatilized residue is redissolved in 1/1 v/v chloroform/cyclohexane (25 ml)
  7. filtrationfiltered
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-ea7b319e062744e88927e53131854903
Source dataset
uspto-grants-1983_09
Patent number
US04404220

Reaction notes

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