反应详情

温度

78 °C

To a stirring solution of 2-(2-methoxyphenyl)oxirane (5.60 g, 37.3 mmol) in toluene (65 mL) was added 4-hydroxybenzaldehyde (6.80 g, 56.0 mmol), 1M NaOH (65 mL) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction was allowed to cool to RT and it was then extracted with EtOAc (2×150 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light oil was adsorbed onto silica gel and chromatographed eluting with 30-40% EtOAc/hexanes to give 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.71 g (17%) the regioisomer as a brown oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 2.05 g (20%) of the title compound as a yellow solid.

1. temperatureto cool to RT
2. extractionit was then extracted with EtOAc (2×150 mL)
3. washThe combined extracts were washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customevaporated in vacuo
7. customchromatographed
8. washeluting with 30-40% EtOAc/hexanes
9. customto give 2 major spots
10. additionFractions containing the higher Rf spot
11. customevaporated in vacuo
12. customto give 1.71 g (17%) the regioisomer as a brown oil
13. additionFractions containing the lower Rf spot
14. customevaporated in vacuo