Reaction #64839

Reaction equation

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

Yield 48.8%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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