Sodium Hydroxide → 4-Diphenylphosphinophenylphosphonic Acid

HRID 2392847Notes

Reaction equation

HRID 2392847 reaction equation
[OH-].[Na+].[C:3]1([P:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]2[CH:15]=[CH:14][C:13]([P:16](=[O:23])([O:20]CC)[O:17]CC)=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O.C1COCC1.Cl>[C:24]1([P:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]2[CH:15]=[CH:14][C:13]([P:16](=[O:17])([OH:20])[OH:23])=[CH:12][CH:11]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 15243843Diethyl [4-(diphenylphosphanyl)phenyl]phosphonate

Product 1

HCID 112678574-Diphenylphosphinophenylphosphonic Acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

0.40 g (10.0 mmol) of NaOH in 7 ml of water are added dropwise at 23° C. to a solution of 2.00 g (5.0 mmol) of diethyl 4-diphenylphosphinophenylphosphonate in 7 ml of THF. After refluxing for 6 hours, the mixture is diluted with a further 7 ml of THF, 4.0 ml of 2N hydrochloric acid are added dropwise at 23° C. and the mixture is stirred for 20 min at 23° C. After phase separation, the aqueous phase is extracted twice, each time with 25 ml of dichloromethane, and the combined organic phases are washed with 25 ml of water. After drying over Na2SO4, complete evaporation on a rotary evaporator and drying under reduced pressure, 1.54 g of 4-diphenylphosphinophenylphosphonic acid (90% of theory) are obtained in the form of a pale yellow solid having an m.p. of 87° C.

Workup

  1. temperatureAfter refluxing for 6 hours
  2. additionare added dropwise at 23° C.
  3. customAfter phase separation
  4. extractionthe aqueous phase is extracted twice
  5. washeach time with 25 ml of dichloromethane, and the combined organic phases are washed with 25 ml of water
  6. dry with materialAfter drying over Na2SO4, complete evaporation on a rotary evaporator
  7. dry with materialdrying under reduced pressure, 1.54 g of 4-diphenylphosphinophenylphosphonic acid (90% of theory)
  8. customare obtained in the form of a pale yellow solid

Sources & evidence

ORD record
ord-fafa1177271940568f49f6fd336a118d
Source dataset
uspto-grants-1998_09
Patent number
US05801263

Reaction notes

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