Реакция #64839

Уравнение реакции

4-methylsulphonyl-2-nitrobenzoyl chloride

triethylamine

5,5-dimethylcyclohexane-1,3-dione

Triethylamine

acetone cyanohydrin

→

2-(4-methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione

Выход 48.8%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture stirred at ambient temperature for 18 hours
2. 2
   ПромывкаThe reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml)
3. 3
   Сушкаdried over magnesium sulphate
4. 4
   Другоеevaporated under reduced pressure
5. 5
   Другоеto give a yellow glass which
6. 6
   Другоеwas recrystallised from methanol (20 ml)

Методика

A solution of 4-methylsulphonyl-2-nitrobenzoyl chloride (9.62 g) in dry dichloromethane (50 ml) was added to a stirred solution of triethylamine (5.6 ml) and 5,5-dimethylcyclohexane-1,3-dione (5 g) in dry dichloromethane (70 ml) during 30 minutes and the reaction mixture stirred at ambient temperature for 4 hours. Triethylamine (15.3 ml) and acetone cyanohydrin (0.5 ml) were added successively and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml), dried over magnesium sulphate and evaporated under reduced pressure to give a yellow glass which was recrystallised from methanol (20 ml) to give 2-(4-methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione (6.4 g), m.p. 156.5°-158° C., as a yellow crystalline solid.

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