1-HYDROXYPYRENE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a RB flask equipped with overhead stirrer, condenser and N2 inlet line with bubbler was added 1-hydroxypyrene (Cambridge Chemical, Inc., 5.0 g, 23 mmol), benzyl bromide (Aldrich, 15.64 g, 92 mmol, 10.94 mL), K2CO3 (Mallinckrodt, 12.72 g, 92 mmol) and acetone (100 mL). The mixture was refluxed overnight, cooled and then poured into H2O (250 mL) and extracted with EtOAc (3×100 mL). The EtOAc layers were combined and washed successively with 1N NaOH (100 mL), H2O (100 mL) and saturated NaCl solution (2×100 mL). The solution was then dried (K2CO3) and the solvent removed by rotary evaporation to give the crude product. This material was purified by passing it through a plug of SiO2 using PhCH3 as the eluting solvent. The solvent was then removed from the appropriate fractions by rotary evaporation and the solid recrystallized from CH2Cl2 /hexane to give 1.78 g (25.9% yield) of 1-benzyloxypyrene, mp 105°-106°, (C,H). To a RB flask equipped with overhead stirrer, condenser and N2 inlet line with bubbler The mixture was refluxed overnight cooled extracted with EtOAc (3×100 mL) washed successively with 1N NaOH (100 mL), H2O (100 mL) and saturated NaCl solution (2×100 mL) The solution was then dried (K2CO3) the solvent removed by rotary evaporation to give the crude product This material was purified The solvent was then removed from the appropriate fractions by rotary evaporation the solid recrystallized from CH2Cl2 /hexane