Bisphenol A → HCID 53652320, compound

Participants

Reaction Steps

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.

Provenance & Evidence