Sodium Hydroxide → 3,3-Diphenylpropanal

Participants

Reaction Conditions

Reaction Steps

4.69 mL (23.55 mmol, 1 eq) of 3,3-diphenyl-1-propanol are dissolved in 100 mL of CH2Cl2 under Ar. 10.5 g (24.73 mmol, 1.05 eq) of Dess Martin Periodinane are added and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluant: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%).

Provenance & Evidence