反应详情

Methanol (0.26 ml, 6.4 mmol) and sodium (0.14 g, 6.1 mmol) were combined in xylene (60 ml) and stirred for 20 min at room temperature. Methyl benzoate (49, 2.47 ml, 19.7 mmol) and acetophenone (0.58 ml, 5.0 mmol) were added and the mixture stirred for 6 hr at 140° C. The mixture was cooled to room temperature and hydrochloric acid (10 ml, 6 N) was added and stirred for 15 min. The resulting mixture was extracted into ethyl acetate, washed twice with water, twice with saturated sodium bicarbonate and twice with water. The ethyl acetate was dried over magnesium sulfate, filtered and evaporated to afford an oil. The crude oil was chromatographed on silica gel with ethyl acetate/hexane to give a solid. The solid was recrystallized from methanol to give 0.71 g (63%) of a pink-orange solid: mp 70-71° C. [expected mp 77-78° C.]; 1H NMR: δ 6.85 (s, 1H), 7.51 (m, 6H), 7.98 (d, 4H, J=6.8 Hz); 13C NMR: δ 93.1, 127.1, 128.6, 132.4, 135.5, 185.6.

1. stirringthe mixture stirred for 6 hr at 140° C
2. temperatureThe mixture was cooled to room temperature
3. stirringstirred for 15 min
4. extractionThe resulting mixture was extracted into ethyl acetate
5. washwashed twice with water, twice with saturated sodium bicarbonate and twice with water
6. dry with materialThe ethyl acetate was dried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customto afford an oil
10. customThe crude oil was chromatographed on silica gel with ethyl acetate/hexane
11. customto give a solid
12. customThe solid was recrystallized from methanol