Bisphenol A → HCID 53652320, compound

HRID 1742555Notes

Reaction equation

HRID 1742555 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 H2 (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. customAn oven-dried 50 ml 3-necked flask is equipped with a magnetic stirring bar
  2. temperaturereflux condenser
  3. temperatureheated
  4. temperatureat reflux for 14 hours
  5. customof partitioning the mixture between Et2O and H2O (50 ml each)
  6. washwashing the organic phase successively with 100 ml portions of H2 (2×), 5 percent HCl (2×), H2O, saturated (2×), H2O and brine
  7. customdrying
  8. filtration(MgSO4) filtration and concentration
  9. customThree consecutive recrystallizations from EtOH-MeOH (2:1)

Sources & evidence

ORD record
ord-819a2005ea084ad6bd1b3b02ceb7fade
Source dataset
uspto-grants-1994_08
Patent number
US05340489

Reaction notes

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