Phenol → 4-[2-(4-Hydroxyphenyl)-2-adamantyl]phenol

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Reaction Conditions

Reaction Steps

2,2-Bis(4-hydroxyphenyl)adamantane (2,2-BPA) was synthesized as an aromatic diol monomer. 2-Adamantanone (4.0 g, 26.6 mmol), phenol (18.74 mL, 213 mmol) and 1-hexanethiol (0.24 mL, 1.69 mmol) were added to a 50-mL 2-bulb flask and stirred at 80° C. After the reactants were completely dissolved, H2SO4 (1.49 mL, 26.6 mmol) was added and reaction was performed under nitrogen flow for 24 hours. After the reaction was completed, the reaction solution was cooled to 50° C. and, after adding to 20 mL of water, extracted 3 times with 40 mL of chloroform. The organic layer was washed 3 times with 40 mL of water and water was removed from the organic layer by adding MgSO4, stirring and filtering. After removing the solvent by distillation under reduced pressure, followed by recrystallization with ethanol, pure 2,2-bis(4-hydroxyphenyl)adamantane (2,2-BPA, yield: 43%) was obtained. Melting temperature was 318° C.

Provenance & Evidence