反应详情

To an alkoxide solution prepared from sodium hydride (60% in oil, 1.60 g, 40.0 mmol) and allyl alcohol (100 mL) was added methyl 4-hydroxymethylbenzoate (3.32 g, 20.0 mmol) under ice-cooling. The resulting mixture was stirred at room temperature for 6 h, adjusted with 1N hydrochloric acid to pH 3, and then concentrated under reduced pressure. To the residue was added ethyl acetate (150 mL), and the mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was separated and purified by silica gel column chromatography (hexane-ethyl acetate, 5:2) to give 3.59 g (93%) of allyl 4-hydroxymethylbenzoate as a pale-yellow oil.

1. temperaturecooling
2. concentrationconcentrated under reduced pressure
3. additionTo the residue was added ethyl acetate (150 mL)
4. washthe mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was separated
8. custompurified by silica gel column chromatography (hexane-ethyl acetate, 5:2)