Phosphoric Acid → HCID 18958216, compound

HRID 1033279Notes

Reaction equation

HRID 1033279 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([P:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1)[CH2:29][Cl:30])([O-:25])=[O:24].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[Cl-:30].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1)[CH2:29][P+:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:22])=[CH:2][CH:3]=1)([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 13956Phosphine, tris(4-methylphenyl)-HCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-

Product 1

HCID 18958216HCID 18958216, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

Into a 50 milliliter glass reactor equipped with a thermometer connected to a temperature controller, a heating mantle, a condenser and a magnetic stirring bar, is charged 5 gms (0.0164 mole) of tri-p-tolyl phosphine and 25 gms of toluene. The slurry is heated to 35° C. then 4.3 gms (0.0199 mole) of 3,5-dinitrobenzyl chloride is added. This reaction mass is heated to 60° C. and maintained at that temperature for 3 hours, then heated to 80° C. and maintained at that temperature for 2 hours, then cooled to 60° C. and maintained at that temperature for 16 hours, then cooed to 26° C. and filtered. The salt is washed with 3 gms of toluene and 3 gms of ethyl acetate and then vacuum dried. There is obtained 3.5 gms of catalyst which has a melting point of >250° C. and a chemical shift of 23.8 ppm (phosphoric acid reference).

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 60° C.
  3. temperaturemaintained at that temperature for 3 hours
  4. temperatureheated to 80° C.
  5. temperaturemaintained at that temperature for 2 hours
  6. temperaturecooled to 60° C.
  7. temperaturemaintained at that temperature for 16 hours
  8. customcooed to 26° C.
  9. filtrationfiltered
  10. washThe salt is washed with 3 gms of toluene and 3 gms of ethyl acetate
  11. customvacuum dried
  12. customThere is obtained 3.5 gms of catalyst which

Sources & evidence

ORD record
ord-4b64a5b810dd4e898f34599bf985ff9f
Source dataset
uspto-grants-1994_05
Patent number
US05310853

Reaction notes

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