Bisphenol A → HCID 53652320, compound

HRID 1590525Notes

Reaction equation

HRID 1590525 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)([CH3:17])[CH3:16]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([O:31][C:28]2[CH:27]=[CH:26][C:25]([C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][S:11]([C:8]4[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)(=[O:13])=[O:12])=[CH:22][CH:23]=3)([CH3:17])[CH3:16])=[CH:30][CH:29]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6623Bisphenol AHCID 1398824-t-Butylbenzenesulfonyl chloride

Product 1

HCID 53652320HCID 53652320, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

An oven-dried 50 ml 3 necked flask is equipped with a magnetic stirring bar and reflux condenser carrying a CaCl2 drying tube and is charged with 4-tert-butylbenzenesulfonyl chloride 9.3 grams (40 mmol), 4,4'-isopropylidenediphenol (4.11 grams, 18 mmol), 4-dimethylaminopyridine 0.11 gram, 0 9 mmol), and anhydrous pyridine (20 ml). and the mixture is stirred and heated at reflux for 14 hours. Workup consists of partitioning the mixture between Et2O and H2O (50 ml each), washing the organic phase successively with 100 ml portions of H2O (2×), 5 percent HCl (2×). H2O, saturated (2×), H2O and brine, then drying (MgSO4). filtration and concentration. This gives 10.41 grams of a pale yellow sold. Three consecutive recrystallizations from EtOH-MeOH (2:1) affords 7.87 grams (70 percent yield) of the title compound as white prisms. m.p. 124° C. to 127° C.

Workup

  1. temperaturereflux condenser
  2. temperatureheated
  3. temperatureat reflux for 14 hours
  4. customof partitioning the mixture between Et2O and H2O (50 ml each)
  5. washwashing the organic phase successively with 100 ml portions of H2O (2×), 5 percent HCl (2×)
  6. dry with materialH2O, saturated (2×), H2O and brine, then drying (MgSO4)
  7. filtrationfiltration and concentration
  8. customThree consecutive recrystallizations from EtOH-MeOH (2:1)

Sources & evidence

ORD record
ord-14e52417e6f0429c9b4923c879f16817
Source dataset
uspto-grants-1993_04
Patent number
US05204011

Reaction notes

Loading…