Phosphoric Acid → HCID 19438174, compound

HRID 1033278Notes

Reaction equation

HRID 1033278 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:25])[CH3:24].P(=O)(O)(O)O>C1(C)C(C)=CC=CC=1>[Br-:25].[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)[CH3:24]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 6332Ethyl Bromide2×HCID 13956Phosphine, tris(4-methylphenyl)-

Product 1

HCID 19438174HCID 19438174, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
30 °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 15 gms (0.0473 mole) of tri-p-tolyl phosphine and 40 gms of xylene. The slurry is heated to 30° C., then 7 gms (0.0642 mole) of ethyl bromide is added. This reaction mass is heated to 45° C. in 1.17 hours and maintained for 21.4 hours, then cooled to 65° C. and maintained for 2.47 hours, then heated to 90° C., then maintained for 2.42 hours at that temperature, then cooled to 25° C. Then 1.5 gm (0.0138 mole) of ethyl bromide is added and maintained at 25° C. for 0.75 hour, then heated to 45° C. and maintained at that temperature for 16.58 hours, then heated to 70° C. and maintained at that temperature for 1.5, then cooled to 48° C. and the resulting phosphonium salt collected by filtration. After vacuum drying, there is obtained 12.8 gms of catalyst which has a melting point of 213°-220° C. and a chemical shift of 24.6 ppm (phosphoric acid reference).

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 45° C. in 1.17 hours
  3. temperaturemaintained for 21.4 hours
  4. temperaturecooled to 65° C.
  5. temperaturemaintained for 2.47 hours
  6. temperatureheated to 90° C.
  7. temperaturemaintained for 2.42 hours at that temperature
  8. temperaturecooled to 25° C
  9. temperaturemaintained at 25° C. for 0.75 hour
  10. temperatureheated to 45° C.
  11. temperaturemaintained at that temperature for 16.58 hours
  12. temperatureheated to 70° C.
  13. temperaturemaintained at that temperature for 1.5
  14. temperaturecooled to 48° C.
  15. filtrationthe resulting phosphonium salt collected by filtration
  16. customAfter vacuum drying
  17. customthere is obtained 12.8 gms of catalyst which

Sources & evidence

ORD record
ord-7dc1c2000ee24f92b6b826ee584a11b3
Source dataset
uspto-grants-1994_05
Patent number
US05310853

Reaction notes

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