反应详情

4-Hydroxy-3-methoxybenzaldehyde (2.1 g, 13.8 mMol) and 3-phenoxypropane-2-one triphenylphosphorane (2.8 g, 6.9 mMol) (prepared as described by LeCorre: C. R. Acad. Sci. Paris, 273 81 (1971)) are dissolved in 100 ml of toluene and warmed to reflux. After three hours, the solvent is evaporated and the residue is taken up in tHF. Sodium bisulfite (10.0 g) is dissolved in 100 ml of water and stirred with the solution for one hour. The THF is evaporated and the water is extracted with chloroform. Drying over magnesium sulfate and evaporation of the chloroform gives a yellow oil. Flash chromatography in ethyl acetate on silica gel gives 1.5 g (65%) of 1-(4'-hydroxy,3'-methoxyphenyl)-4-phenoxy-1-butene-3-one; mp=85°-87° C. C, H analysis Calcd for C17H16O4 (71.81, 5.68); Found (71.85, 5.50).

1. temperaturewarmed to reflux
2. customthe solvent is evaporated
3. dissolutionSodium bisulfite (10.0 g) is dissolved in 100 ml of water
4. customThe THF is evaporated
5. extractionthe water is extracted with chloroform
6. dry with materialDrying over magnesium sulfate and evaporation of the chloroform
7. customgives a yellow oil