Réaction #64839

Équation de réaction

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

Rendement 48.8%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source