4,4'-Dihydroxybiphenyl → HCID 88020563, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 28.7 g (0.15 mol) of 4,4′-bisphenol in 75 mL of DMSO was placed into a 500 mL round-bottom flask. The solution was purged with nitrogen gas at room temperature (23° C.) for 2-3 hours. Then, 140.85 mL of 2.13M (0.300 mol) of standardized aq KOH was added dropwise to the solution in the flask, while the flask rested in an ice-bath and the nitrogen gas purge continued. After the KOH solution was added, the reaction mixture was heated to 100° C. and stirred for 1 day, followed by distilling off most of the water. The remaining solvent was evaporated off slowly under reduced pressure (10 torr). The reaction product was then dried thoroughly at 140-150° C. with fill vacuum (10−2 torr) for at least 2 days. Then, a solution of 104 g (0.4 mol) of 1,2-dibromotetrafluoroethane in 100 mL of well-dried DMSO was transferred to the flask via a closed system. The mixture was stirred at 35-40° C. for 4 days, followed by filtration to remove the solid precipitate. The precipitate was washed with acetone three times. The combined acetone solution was then washed in a separatory fimnel, first with a 5% sodium bicarbonate water solution, then with 0.1N HCl, and finally washed with distilled water and dried over sodium sulfate overnight. After removing solid material by filtration and evaporating the solvents at reduced pressure (10 torr), the crude product was purified by sublimation with an oil bath at a temperature around 100-110° C. A product of 75 g (0.137 mol) of 4,4-di(2-bromotetrafluoroethoxy)biphenyl was obtained at a yield of 91%. The amount of hydrogen by-product in the fmal product was around 1%.

Provenance & Evidence