Hydrochloric Acid → 4,4'-Bis(4-hydroxyphenyl thio)biphenyl

Participants

Reaction Steps

Potassium carbonate (75.9 g, 0.55 mol) was charged to a 2 liter flask equipped with a stirrer, condenser, dropping funnel, thermometer and nitrogen purge. Dimethylformamide (200 ml) was added and the solution heated to 80°-90° C. 4-mercaptophenol (69.3 g, 0.55 mol) in 200 ml of dimethylformamide was added to the stirred reaction mixture over one hour. The reaction mixture was maintained at 100°-110° C. for two hours. Solid 4,4'-dibromobiphenyl (78 g, 0.25 mol) was then added over one hour. The reaction mixture was refluxed for 18 hours, cooled to room temperature, and poured into 10% HCl. The white to yellow solid was collected with suction and washed with water. The solid was treated with 5-10% NaOH and filtered once more with suction. The mother liquor was acidified to pH≈2 and the solid collected and recyrstallized from chlorobenzene/methanol. A 34% yield of pure HPSB was obtained having a melting point of 214°-217° C.

Provenance & Evidence