Reacción #10797

Ecuación de reacción

sulfuric acid

acetyl chloride

aluminum chloride

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

→

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

Rendimiento 47.0%

Disolventes

carbon disulfide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for 2 hours
2. 2
   workup.ADDITIONpoured into ice
3. 3
   OtroThe mixture was partitioned
4. 4
   ExtracciónThe aqueous layer was extracted with ethyl acetate
5. 5
   LavadoThe solution of ethyl acetate was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude product was purified by flash chromatography
9. 9
   LavadoElution with ethyl acetate (33%, v/v, in hexane)

Procedimiento

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).

Fuente