反应详情

A solution of racemic 1,3-diphenyl-1-propanol (1.26 g; 5.94 mmol) was dissolved in 10 mL of acetone, and Jones reagent was added until persistence of the orange color. After stirring for 30 min, the reaction was quenched by adding 2 mL of 2-propanol. The solvent was decanted away from the precipitated solids, which were washed with ethyl acetate. The combined organic fractions were washed with 2×20 mL of water, dried and concentrated. The crude product was filtered through a plug of silica gel, eluting with 25% ethyl acetate/hexane, to obtain 1.07 g (86%) of 1,3-diphenylpropanone as a white crystalline solid, 1H NMR (360 Mhz; CDCl3): d 3.09 (t, 2H, J=8.1); 3.33 (t, 2H, J8.1); 7.29 (m, 5H); 7.49 (m, 3H); 7.98 (m, 2H).

1. customthe reaction was quenched
2. additionby adding 2 mL of 2-propanol
3. customThe solvent was decanted away from the precipitated solids, which
4. washwere washed with ethyl acetate
5. washThe combined organic fractions were washed with 2×20 mL of water
6. customdried
7. concentrationconcentrated
8. filtrationThe crude product was filtered through a plug of silica gel
9. washeluting with 25% ethyl acetate/hexane