Phosgene → 2,2-Diphenyl-ethyl chloroformate

Participants

Reaction Conditions

Reaction Steps

To a solution of 7.0 g (35.4 mmol) of the alcohol (12) in 50 mL toluene at 0 degrees C., was slowly added 100 mL phosgene in toluene (12.5% phosgene in toluene). The reaction mixture was stirred at 0 degrees C. for 30 minutes and then at room temperature for 2 hours. The excess reagent and solvent was removed under reduced pressure and the crude product was quickly passed through a pad of silica gel (silica gel, CH2Cl2 -Hexane 2:3) to yield 7.8 g (80%) of the chloroformate (13). DCI-NH3 -MS, m/z (relative intensity), 259 (M+, 55); 1H-NMR (CDCl3, 300 MHz) 7.28 (m, 10H), 4.83 (d, 2H, J=7.5 Hz), and 4.45 (t, 1H, J=7.5 Hz).

Provenance & Evidence