반응 #164867

반응 방정식

Methanol

sodium

Methyl benzoate

acetophenone

hydrochloric acid

→

pink-orange solid

수율 63.3%

1,3-Diphenylpropane-1,3-dione

수율 63.3%

용매

xylene

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 6 hr at 140° C
2. 2
   온도The mixture was cooled to room temperature
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   추출The resulting mixture was extracted into ethyl acetate
5. 5
   세척washed twice with water, twice with saturated sodium bicarbonate and twice with water
6. 6
   건조The ethyl acetate was dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to afford an oil
10. 10
    기타The crude oil was chromatographed on silica gel with ethyl acetate/hexane
11. 11
    기타to give a solid
12. 12
    기타The solid was recrystallized from methanol

실험 절차

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.

출처