Phosphoric Acid → HCID 18958236, compound

HRID 2379257Notes

Reaction equation

HRID 2379257 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.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][Cl:29].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[Cl-:29].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][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

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 13956Phosphine, tris(4-methylphenyl)-HCID 699943-Methoxybenzyl chloride

Product 1

HCID 18958236HCID 18958236, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °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 maintained at 25° C. then 3 gms (0.0191 mole) of 3-methoxybenzyl chloride is added. This reaction mass is maintained at 25° C. for 15 hours, then heated to 70° C. and maintained for 2 hours, then cooled to 90° C. and maintained for 2 hours, then cooled to 70° C. and the resulting phosphonium salt collected by filtration. The salt is washed with 5 gms of toluene then vacuum dried. There is obtained 1.2 gms of catalyst which has a melting point of >250° C. and a chemical 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 maintained at 25° C. for 15 hours
  3. temperatureheated to 70° C.
  4. temperaturemaintained for 2 hours
  5. temperaturecooled to 90° C.
  6. temperaturemaintained for 2 hours
  7. temperaturecooled to 70° C.
  8. filtrationthe resulting phosphonium salt collected by filtration
  9. washThe salt is washed with 5 gms of toluene
  10. customvacuum dried
  11. customThere is obtained 1.2 gms of catalyst which

Sources & evidence

ORD record
ord-60584bb6cb164e65ba5b354f6e9accce
Source dataset
uspto-grants-1994_11
Patent number
US05360886

Reaction notes

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