Hydrochloric Acid → 1,3-Bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane

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Reaction Steps

A mixture of 2.00 g (6.26 mmol) of 1,3-bis(4-hydroxyphenyl)adamantane, 2.00 g (12.7 mmol) of 5-fluoro-2-nitrophenol, 1.70 g (12.3 mmol) of anhydrous K2CO3, and 50 mL of dry DMF was reflux for 12 h under nitrogen. The mixture was allowed to cool and subsequently poured into 500 mL of distilled water. The resulting solution was acidied by concentrated hydrogen chloride to PH=3.5˜4.0. The precipitated product was collected, washed thoroughly with water until neutral, and then dried to give 3.46 g (93.1%) of 1,3-bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane. mp 118˜122° C.; Elemental Anal. Calcd. for C34H30N2O8: C, 68.69; H, 5.05; N, 4.71. Found: C, 68.56; H, 5.12; N, 4.65. MS (EI) m/z 594 (M+, 100); IR (KBr): 3416, 2890, 2857, 1556, 1342 cm−1.

Provenance & Evidence