5-Phenyl-1-pentanol → Benzenepentanal

Participants

Reaction Steps

To a solution of 5-phenylpentanol (5 g, 30.4 mmol), NaBr (3.2 g, 31.3 mmol), and TEMPO® (48 mg, 0.3 mmol) in EtOAc (60 mL), toluene (60 mL), and water (9 mL), cooled to 0° C., is added portionwise (50 mL) over 30 minutes a solution containing NaOCl (0.35 M in H2O, 287 mL, 100.4 mmol) and NaHCO3 (22.2 g, 264.8 mmol). The reaction is quenched by the addition of EtOH (10 mL). The biphasic mixture is separated and the organic phase is washed with aqueous Na2S2O3 (2×100 mL), brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated to afford crude 5-phenylpentanal which is homogeneous by TLC analysis [hexane/EtOAc, 4:1, Rf (5-phenylpentanol)=0.30; Rf (5-phenylpentanal)=0.65] and used without further purification.

Provenance & Evidence