Sodium Hydroxide → HCID 178527046, compound

HRID 2392845Notes

Reaction equation

HRID 2392845 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][CH:13]=[CH:12][C:11]=2[CH2:16][PH:17](=[O:23])[O:18]CC(C)C)[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][CH:13]=[CH:12][C:11]=2[CH2:16][PH:17](=[O:18])[OH:23])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 178454797HCID 178454797, compound

Product 1

HCID 178527046HCID 178527046, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

0.30 g (7.6 mmol) of NaOH in 5 ml of water are added dropwise at 23° C. to a solution of 1.50 g (3.8 mmol) of isobutyl (2-diphenylphosphinophenyl)methylphosphinate in 5 ml of THF. After refluxing for 6 hours, the mixture is diluted with a further 5 ml of THF, 3.0 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 20 ml of dichloromethane, and the combined organic phases are washed with 20 ml of water. After drying over Na2SO4, complete evaporation under reduced pressure and drying in high vacuum, 1.17 g of (2-diphenylphosphinophenyl)methylphosphinic acid (92% of theory) are obtained in the form of a pale yellow solid having an m.p. of 167° 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 20 ml of dichloromethane, and the combined organic phases are washed with 20 ml of water
  6. dry with materialAfter drying over Na2SO4, complete evaporation under reduced pressure
  7. dry with materialdrying in high vacuum, 1.17 g of (2-diphenylphosphinophenyl)methylphosphinic acid (92% of theory)
  8. customare obtained in the form of a pale yellow solid

Sources & evidence

ORD record
ord-a3f7dcd68eee4f74aadb6318791ca2d3
Source dataset
uspto-grants-1998_09
Patent number
US05801263

Reaction notes

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