反应详情

To a solution of 53.6 g (0.20 mole) of 2-allyloxy-4-(benzyloxy)benzaldehyde in 500 mL of methylene chloride was added a solution of 90 g (˜0.3 mole) of 57-86% m-chloroperoxybenzoic acid in 500 mL of methylene chloride. The mixture was stirred at room temperature for 3 days. It was then diluted to 2 L with methylene chloride and washed four times with 500 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum to a brown oil. This was redissolved in 1 L of methanol, 110 g of basic alumina added and the mixture stirred at room temperature for 15 hours. The alumina was removed by filtration and the filtrate concentrated to 50 g of a yellow solid. The crude solid was column chromatographed on silica gel with hexane/methylene chloride as eluant to give 33 g of the title compound as a white solid, m.p. 62° C.

1. washwashed four times with 500 mL portions of saturated aqueous sodium bicarbonate
2. dry with materialdried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuum to a brown oil
5. dissolutionThis was redissolved in 1 L of methanol
6. addition110 g of basic alumina added
7. stirringthe mixture stirred at room temperature for 15 hours
8. customThe alumina was removed by filtration
9. concentrationthe filtrate concentrated to 50 g of a yellow solid
10. customchromatographed on silica gel with hexane/methylene chloride as eluant