Hydrochloric Acid → HCID 19387648, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-mercaptophenol (50g, 0.317 mol for 80% purity), anhydrous potassium carbonate (46.9 9, g. 0.34 mol) and 150 mL of DMF was stirred and heated under nitrogen at 110°-120° C. for 90 min. The mixture was cooled to 80° C., a suspension of 4,4'-dichloro-benzophenone (40.1 g, 0.16 mol) in 100 mL DMF was added over 5 min and the mixture was stirred and heated under reflux for 4 h. After cooling to room temperature, there was added 400 mL of water and enough conc. HCl to adjust the pH to ca. 2. After stirring for 1 h, the pale yellow solid was filtered, washed with water and recrystallized from aqueous ethanol to afford 4,4'-bis(4-hydroxyphenylthio)benzo-phenone as pale yellow microcrystals, 59 g (86% yield), mp 219°-221° C. 1H NMR (DMSO-d6) was consistent with the structure with a sharp singlet for OH at δ 10.02 and four sets of doublets for the aromatic protons ranging from δ 7.61 to 6.99.

Provenance & Evidence