反应详情

温度

55 °C

A solution of (2,4,6-trimethylphenyl)furan-2-ylmethanol (27.8 g, 129 mmol) in acetone (730 ml) and water (100 ml) is heated to 55° C. and polyphosphoric acid (2 g) is added. The mixture is stirred at 55° C. for 7 hours, then cooled to room temperature overnight. The reaction mixture is concentrated under reduced pressure to remove most of the acetone then ethyl acetate (500 ml) is added, and the reaction mixture is partitioned. The aqueous phase is extracted into ethyl acetate and the organic solutions are combined, washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone.

1. temperaturecooled to room temperature overnight
2. concentrationThe reaction mixture is concentrated under reduced pressure
3. customto remove most of the acetone
4. additionethyl acetate (500 ml) is added
5. customthe reaction mixture is partitioned
6. extractionThe aqueous phase is extracted into ethyl acetate
7. washwashed with saturated aqueous sodium bicarbonate solution and brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate is concentrated under reduced pressure
11. customThe residue is purified by column chromatography on silica gel