Reacción #164867

Ecuación de reacción

Methanol

sodium

Methyl benzoate

acetophenone

hydrochloric acid

→

pink-orange solid

Rendimiento 63.3%

1,3-Diphenylpropane-1,3-dione

Rendimiento 63.3%

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente