Реакция #10797

Уравнение реакции

sulfuric acid

acetyl chloride

aluminum chloride

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

→

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

Выход 47.0%

Растворители

carbon disulfide

Условия реакции

Обработка

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

Методика

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).

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