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Bisphenol S → Bis[4-(diphenylphosphinyloxy)phenyl] Sulfone

HRID 273672
Notes
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Reaction equation

HRID 273672 reaction equation
[S:1]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:18]1([P:24](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]1([P:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([O:10][C:7]2[CH:8]=[CH:9][C:4]([S:1]([C:11]3[CH:16]=[CH:15][C:14]([O:17][P:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:25])=[CH:13][CH:12]=3)(=[O:3])=[O:2])=[CH:5][CH:6]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6626Bisphenol SHCID 73910Diphenylphosphinic chloride

Product 1

HCID 10974311Bis[4-(diphenylphosphinyloxy)phenyl] SulfoneYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

An oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser carrying a CaCl2 -Drierite drying tube, and a heating mantle, was charged with 4,4'-sulfonyldiphenol (3.9 g, 15.6 mmol), 4-dimethylaminopyridine (0.39 g, 3.2 mmol), and anhydrous pyridine (35 mL), and the stirred solution was treated slowly with diphenylphosphinyl chloride (6.5 mL, 34.1 mmol) via syringe. The resulting mixture was heated at reflux for 7 hours, then was allowed to stand at room temperature for 16 hours. The reaction was monitored periodically by HPLC. After completion of the reaction, the mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL), and the organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine, then it was dried (MgSO4), filtered and concentrated leaving a white solid residue. Recrystallization from ethyl acetate-THF (9:1) afforded 9.5 g (94 percent yield) of the title compound as a white fluffy solid, m.p. 210-211° C. which had a PDSC (O2) onset/extrap (° C.) of 376/397.

Workup

  1. customAn oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 7 hours
  4. customAfter completion of the reaction
  5. customthe mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL)
  6. washthe organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine
  7. dry with materialit was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customleaving a white solid residue
  11. customRecrystallization from ethyl acetate-THF (9:1)

Sources & evidence

ORD record
ord-ca40cad95bd44aa0b580fad5583761b7
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387353

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes