反应详情

温度

-20 °C

The procedure in J. Org. Chem. 1995, 50, 888-890 was followed. Briefly, a solution of quinic acid (20.0 g, 0.104 mol), benzaldehyde (16.6 g, 156 mmol) and para-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol) in toluene (350 mL) was refluxed for 10 hours in a flask equipped with a Dean-Stark trap. The reaction mixture was cooled, washed with saturated NaHCO3 solution and brine, dried (MgSO4). Filtered and concentrated. The concentrate was dissolved in 1:1 hexanes/ethyl acetate (100 mL) and cooled to −20° C. for 2 hours to provide 10.8 g (40%) of the desired product.

1. customequipped with a Dean-Stark trap
2. temperatureThe reaction mixture was cooled
3. washwashed with saturated NaHCO3 solution and brine
4. dry with materialdried (MgSO4)
5. filtrationFiltered
6. concentrationconcentrated
7. dissolutionThe concentrate was dissolved in 1:1 hexanes/ethyl acetate (100 mL)