反应详情

温度

100 °C

Hinokitiol (20 g, 0.12 mol) and potassium hydroxide (8 g, 0.12 mol) were dissolved in water (80 ml), and 37% Formalin (12 ml, 0.16 mmol) was added thereto. The reaction solution was heated at 100° C. for 5 hours while stirring. The reaction solution was neutralized with 6N HCl, then the reaction product was extracted with dichloromethane. The extract was dried over sodium sulfate, then concentrated under reduced pressure. The residue was dissolved in acetone (200 ml), potassium carbonate (34 g, 0.25 mol) and dimethyl sulfate (16 ml, 0.16 mol) were added thereto, and the solution was heated and refluxed for an hour with stirring. The precipitate was removed by filtration, and filtrate was concentrated under reduced pressure. The filtration residue was washed with dichloromethane. The resultant was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography [(eluent:hexane/ethyl acetate (1:4)] to give 18.5 g of 7-hydroxymethyl-4-isopropyl-2-methyoxy-2,4,6-cycloheptatrien-1-one as a pale yellow oil (yield, 74%). This oil was solidified when allowed to stand at room temperature.

1. extractionthe reaction product was extracted with dichloromethane
2. dry with materialThe extract was dried over sodium sulfate
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in acetone (200 ml)
5. temperaturethe solution was heated
6. temperaturerefluxed for an hour
7. stirringwith stirring
8. customThe precipitate was removed by filtration, and filtrate
9. concentrationwas concentrated under reduced pressure
10. washThe filtration residue was washed with dichloromethane
11. washThe resultant was washed with water
12. dry with materialdried over sodium sulfate
13. distillationThe solvent was distilled off under reduced pressure
14. customthe residue was purified by silica gel column chromatography [(eluent
15. customhexane/ethyl acetate (1:4)] to give