Bisphenol A → HCID 20093770, compound

HRID 273671Notes

Reaction equation

HRID 273671 reaction equation
[Cl-].[Cl-].[Ca+2].[O-]S([O-])(=O)=O.[Ca+2].[C:10]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)([CH3:12])[CH3:11].[C:27]1([P:33](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:27]1([P:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([O:26][C:23]2[CH:22]=[CH:21][C:20]([C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][P:33]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:34])=[CH:17][CH:18]=3)([CH3:12])[CH3:11])=[CH:25][CH:24]=2)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 6623Bisphenol AHCID 73910Diphenylphosphinic chlorideHCID 131718843HCID 131718843, compound

Product 1

HCID 20093770HCID 20093770, compoundYield 92%

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 tuber and a heating mantle, was charged with 4,4'-isopropylidenediphenol (3.6 g, 15.8 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;250 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 on the rotavap to leave 9.42 g of a faintly yellowish thick oil which set on standing to a brittle glassy material. Crystallization was effected by dissolving the material in a minimum amount of EtOAc with heating then diluting the solution with hexane and allowing it to stand in a freezer at -25° C. overnight. This afforded 9.1 g (92 percent yield) of the title compound as white prisms, m.p. 71-72° C. which had a PDSC (O2) onset/extrap (° C.) of 316/347.

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;250 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 on the rotavap
  10. customto leave 9.42 g of a faintly yellowish thick oil which
  11. customCrystallization
  12. dissolutionby dissolving the material in a minimum amount of EtOAc
  13. temperaturewith heating
  14. additionthen diluting the solution with hexane
  15. waitto stand in a freezer at -25° C. overnight

Sources & evidence

ORD record
ord-0b319ce0689b40d4847847189908b28e
Source dataset
uspto-grants-1995_02
Patent number
US05387353

Reaction notes

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