Phosphoric Acid → HCID 18958190, compound

HRID 2379253Notes

Reaction equation

HRID 2379253 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.[CH2:23]([Br:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.P(=O)(O)(O)O>C1(C)C=CC=CC=1>[Br-:30].[CH2:23]([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)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 7498Benzyl BromideHCID 13956Phosphine, tris(4-methylphenyl)-

Product 1

HCID 18958190HCID 18958190, 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 5.39 gms, (0.0177 mole) of tri-p-tolyl phosphine and 23 gms of toluene. The slurry is heated to 35° C., then 3.6 gms (0.0211 mole) of benzyl bromide is added. This reaction mass is heated to 40° C. in 0.25 hour and maintained for 4 hours, then cooled to 29° C. and the resulting phosphonium salt collected by filtration. The salt is washed with 25 gms of toluene then vacuum dried. There is obtained 6.7 gms of catalyst which has a melting point of >250° C. and a chemcial shift of 22.1 ppm (phosphoric acid reference).

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 40° C. in 0.25 hour
  3. temperaturemaintained for 4 hours
  4. temperaturecooled to 29° C.
  5. filtrationthe resulting phosphonium salt collected by filtration
  6. washThe salt is washed with 25 gms of toluene
  7. customvacuum dried
  8. customThere is obtained 6.7 gms of catalyst which

Sources & evidence

ORD record
ord-6a67d46a31e04d2f8a4e35b6941b3c4b
Source dataset
uspto-grants-1994_11
Patent number
US05360886

Reaction notes

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