Water → [4-(Benzenesulfonyl)phenyl]phenylphosphinic acid

HRID 2398927Notes

Reaction equation

HRID 2398927 reaction equation
F[B-](F)(F)F.[C:6]1([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+]#N)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[P:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH2:32].C(OCC)(=[O:35])C>[OH-].[Na+].[Cu]Cl>[C:25]1([P:24]([C:18]2[CH:19]=[CH:20][C:15]([S:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:14])=[O:13])=[CH:16][CH:17]=2)(=[O:35])[OH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12573Phenyl phosphorus dichlorideHCID 20360589HCID 20360589, compound

Product 1

HCID 20360606[4-(Benzenesulfonyl)phenyl]phenylphosphinic acidYield 45%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a slurry of 44 g (0.13 mole) of 4-(phenylsulfonyl) benzenediazonium tetrafluoroborate in 400 ml of ethyl acetate was added 22.8 ml (0.17 mole)of dichlorophenylphosphine and 0.5 g of copper (I) chloride. After the reaction had been stirred for two hours at room temperature with no apparent change, it was heated to 30° C. (this reaction can be vigorous and care should be used). Evolution of gas occurred, and the solid dissolved. Heating was continued for 1.5 hr., the mixture was then cooled, and 125 ml of water was added. The ethyl acetate and volatile by-products were removed by steam distillation, and then the aqueous residue was cooled and filtered to give a solid that, while still wet, wasdissolved in approximately 2 liters of dilute sodium hydroxide. The resulting solution was filtered to remove insoluble non-acidic material and acidified with hydrochloric acid to give 36 g (80%) of crude product, m.p. 220°-4° C. This material was crystallized from 80% ethanol to give 20 g (45%) of phenyl[4-(phenylsulfonyl)phenyl]phosphinic acid. m.p. 225°-8° C. Anal. Calcd. for C18H15O4PS: C, 60.3; H, 4.23; P, 8.64; S, 8.95. Found: C, 60.2; H, 4.49; P, 8.77; S, 9.49.

Workup

  1. temperaturewas heated to 30° C. (
  2. customthis reaction
  3. dissolutionthe solid dissolved
  4. temperatureHeating
  5. waitwas continued for 1.5 hr
  6. temperature, the mixture was then cooled
  7. customThe ethyl acetate and volatile by-products were removed by steam distillation
  8. temperaturethe aqueous residue was cooled
  9. filtrationfiltered
  10. customto give a solid that, while still wet,
  11. filtrationThe resulting solution was filtered
  12. customto remove insoluble non-acidic material
  13. customto give 36 g (80%) of crude product, m.p. 220°-4° C
  14. customThis material was crystallized from 80% ethanol

Sources & evidence

ORD record
ord-e5ccf79468a140628ccdb9d28763b5fc
Source dataset
uspto-grants-1977_05
Patent number
US04026830

Reaction notes

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