반응 #10797

반응 방정식

sulfuric acid

acetyl chloride

aluminum chloride

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

→

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

수율 47.0%

용매

carbon disulfide

반응 조건

후처리

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

실험 절차

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).

출처