反応 #4075

反応方程式

ethyl acetoacetate

mesityl oxide

heptane

→

ester

収率 27.0%

Ethyl 4-Oxo-2,6,6-Trimethylcyclohex-2-Ene-1-Carboxylate

収率 27.0%

溶媒

toluene

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux in a 5000 ml round bottom flask
3. 3
   その他The flask was equipped with a Dean-Stark trap
4. 4
   その他drying tube
5. 5
   workup.ADDITIONan additional 25 g of zinc chloride was added
6. 6
   温度refluxing
7. 7
   workup.WAITcontinued for 36 h
8. 8
   温度After cooling
9. 9
   洗浄the reaction mixture was washed with 1500 ml of water, 5% sodium bicarbonate solution (2×1000 ml)
10. 10
    その他Removal of solvent
11. 11
    その他by evaporation
12. 12
    その他yielded 979 g of crude product
13. 13
    workup.DISTILLATIONDistillation of the crude product

実験手順

A mixture of 1020 ml (1041 g, 8.00 mol) of ethyl acetoacetate, 960 ml (824 g, 8.40 mol) of mesityl oxide, 1000 ml of heptane, 600 ml of toluene, and 175 g of zinc chloride was heated at reflux in a 5000 ml round bottom flask while stirring. The flask was equipped with a Dean-Stark trap and drying tube. After 24 h, an additional 25 g of zinc chloride was added and refluxing continued for 36 h. After cooling, the reaction mixture was washed with 1500 ml of water, 5% sodium bicarbonate solution (2×1000 ml), and another 1500 ml of water. Removal of solvent by evaporation yielded 979 g of crude product. Distillation of the crude product provided 453.5 g of the desired ester which represents 27.0% yield. Distillation was at 124°-5° C. (3.0 torr).

出典