Phosphoric Acid → HCID 18958205, compound

HRID 1033283Notes

Reaction equation

HRID 1033283 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[P:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].[CH2:23]([I:25])[CH3:24].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[I-:25].[CH2:23]([P+:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:22])[CH3:24]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 6340IodoethaneHCID 80271Tri-o-tolylphosphine

Product 1

HCID 18958205HCID 18958205, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
27 °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-o-tolyl phosphine and 23 gms of toluene. The slurry is heated to 27° C., then 3.08 gms (0.0177 mole) of ethyl iodide is added. This reaction mass is heated to 70° C. and maintained at that temperature for 17 hours, then heated to 100° C. and maintained at that temperature for 9 hours, then cooled to 70° C. and maintained at that temperature for 15 hours, then cooled to 26° C. and the resulting phosphonium salt collected by filtration. The salt is washed with 6 gms of toluene then vacuum dried. There if obtained 1.6 gms of catalyst which has a melting point of 247°-250° C. and a chemical shift of 28.5 ppm (phosphoric acid reference).

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 70° C.
  3. temperaturemaintained at that temperature for 17 hours
  4. temperatureheated to 100° C.
  5. temperaturemaintained at that temperature for 9 hours
  6. temperaturecooled to 70° C.
  7. temperaturemaintained at that temperature for 15 hours
  8. temperaturecooled to 26° C.
  9. filtrationthe resulting phosphonium salt collected by filtration
  10. washThe salt is washed with 6 gms of toluene
  11. customvacuum dried
  12. customThere if obtained 1.6 gms of catalyst which

Sources & evidence

ORD record
ord-207370925be34ec788dd201bf978cc0e
Source dataset
uspto-grants-1994_05
Patent number
US05310853

Reaction notes

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