反应 #10797

反应方程式

sulfuric acid

acetyl chloride

aluminum chloride

2-methyl-2-phenyl-propionic acid ethyl ester

→

2-(4-acetyl-phenyl)-2-methyl-propionic acid ethyl ester

收率 47.0%

溶剂

carbon disulfide

反应条件

后处理

1. 1
   温度The reaction mixture was refluxed for 2 hours
2. 2
   workup.ADDITIONpoured into ice
3. 3
   其他The mixture was partitioned
4. 4
   萃取The aqueous layer was extracted with ethyl acetate
5. 5
   洗涤The solution of ethyl acetate was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine
6. 6
   干燥dried over sodium sulfate
7. 7
   浓缩concentrated
8. 8
   其他The crude product was purified by flash chromatography
9. 9
   洗涤Elution with ethyl acetate (33%, v/v, in hexane)

实验过程

Ex-77A: To a mixture of aluminum chloride (2.8 g, 20.8 mmol) in carbon disulfide (50 mL) was added acetyl chloride (0.74 mL, 10.4 mmol) followed by addition of 2-methyl-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 mmol). The reaction mixture was refluxed for 2 hours and then poured into ice containing sulfuric acid (6M). The mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (33%, v/v, in hexane) gave 2-(4-acetyl-phenyl)-2-methyl-propionic acid ethyl ester (0.57 g, 47%). 1H NMR (CDCl3) δ 7.92 (d, J=7.6 Hz, 2H), 7.42 (d, J=7.6 Hz, 2H), 4.13 (q, J=7.2 Hz, 2H), 2.59 (s, 3H), 1.61 (s, 3H), 1.59 (s, 3H), 1.18 (t, J=7.2 Hz, 3H).

来源