反应详情

4-allylphenol (8.9 g, 66.3 mmol) was dissolved in CH2Cl2 (180 ml). After addition of NaHCO3 (8.4 g, 99.5 mmol), m-chloroperbenzoic acid 70% (18 g, 73 mmol) was added portionwise. After 6 hours at room temperature, additional NaHCO3 (8.4 g, 99.5 mmol) and m-chloroperbenzoic acid 70% (18 g, 73 mmol) were added. After 17 hours, the reaction mixture was washed with sat. NaHCO3 (200 ml) and the resulting aqueous phases were extracted with CH2Cl2 (3×10 ml). The combined organic phases were washed with sat. Na2S2O3 (2×100 ml), dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexan-ethyl acetate 9:1 then 1:1) to provide (RS)-4-oxiranylmethyl-phenol (3.77 g, 38%) as yellow solid, m.p. 54°-57° C. and MS: m/e=150 (M+).

1. additionwas added portionwise
2. waitAfter 17 hours
3. washthe reaction mixture was washed with sat. NaHCO3 (200 ml)
4. extractionthe resulting aqueous phases were extracted with CH2Cl2 (3×10 ml)
5. washThe combined organic phases were washed with sat. Na2S2O3 (2×100 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe residue was chromatographed over silica gel (hexan-ethyl acetate 9:1