Phosphoric Acid → HCID 18958222, compound

HRID 2379259Notes

Reaction equation

HRID 2379259 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.[Br:23][CH2:24][CH2:25][CH2:26][OH:27].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[Br-:23].[OH:27][CH2:26][CH2:25][CH2:24][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 123083-Bromo-1-propanolHCID 13956Phosphine, tris(4-methylphenyl)-

Product 1

HCID 18958222HCID 18958222, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °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 5.19 gms (0.0171 mole) of tri-p-tolyl phosphine and 23 gms of toluene. The slurry is heated to 40° C., then 2.85 gms (0.0205 mole) of 3-bromo-1-propanol is added. This reaction mass is heated to 40° C. in 1.2 hours, then increased the temperature to 80° C. and maintained at that temperature for 1 hour, then increased the temperature to 100° C. and maintained at that temperature for 1.75 hours, then cooled to 30° C., and then separated. The salt is washed with 10 gms of toluene, decanted and then vacuum dried. There is obtained 5.24 gms of an oily catalyst which has a chemical shift of 23.3 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 1.2 hours
  3. temperatureincreased the temperature to 80° C.
  4. temperaturemaintained at that temperature for 1 hour
  5. temperatureincreased the temperature to 100° C.
  6. temperaturemaintained at that temperature for 1.75 hours
  7. temperaturecooled to 30° C.
  8. customseparated
  9. washThe salt is washed with 10 gms of toluene
  10. customdecanted
  11. customvacuum dried
  12. customThere is obtained 5.24 gms of an oily catalyst which

Sources & evidence

ORD record
ord-2bca0adb6e944247934d1635272423f3
Source dataset
uspto-grants-1994_11
Patent number
US05360886

Reaction notes

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