Oxygen → 1,3-Diphenyl-2-propanol

Participants

Reaction Steps

258 mg (1 mmol) of (dibenzyl)acetyl chloride in 1 ml of toluene are added at room temperature to 140 mg (1.1 mmol) of N-hydroxypyridine-2-thione and 0.1 ml of pyridine in 5 ml of toluene. The mixture is maintained with stirring for 30 minutes. The filtered solution is added dropwise during 20 minutes to 1 ml of t-butylmercaptan in 20 ml of toluene at 80° C., and a vigorous stream of oxygen is passed into this solution. The reaction is continued for 1 hour at 80° C., and the reaction mixture is then stirred for 2 hours at room temperature before being poured into 10 ml of a saturated solution of potassium carbonate. The organic phase is again washed twice with potassium carbonate (2×10 ml), then with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate, filtered and evaporated to dryness. The crude product obtained is filtered on silica (100% CH2Cl2) to give 174 mg of the corresponding hydroxylated derivative. Yield 82%.

Provenance & Evidence